Handbook of Hydroxybenzophenones by Robert Martin formerly of the Institut Curie, Paris, France KLUWER ACADEMIC PUBLISHERS DORDRECHT / BOSTON / LONDON A CLP Catalogue record for this book is available from the Library of Congress ISBN 0-7923-6507-0 Published by Kluwer Academic Publishers, P.O Box 17, 3300 AA Dordrecht, The Netherlands Sold and distributed in North, Central and South America by Kluwer Academic Publishers, 101 Philip Drive, Norwell, MA 02061, U.S.A In all other countries, sold and distributed by Kluwer Academic Publishers, P.O Box 322, 3300 AH Dordrecht, The Netherlands Printed on acid-free paper All Rights Reserved © 2000 Kluwer Academic Publishers No part of the material protected by this copyright notice may be reproduced or utilized in any form or by any means, electronic or mechanical, including photocopying, recording or by any information storage and retrieval system, without written permission from the copyright owner Printed in the Netherlands To my dear Angele, always so touchingly devoted to me throughout these many years She reminds me every day of the sweet title of this song by Jean Ferrat: "What would I be without you?" Robert MARTIN PREFACE Two centuries of organic chemistry have already yielded millions of molecules, either synyhesized or isolated as natural products created by biosynthesis, but much still remains to be done Therefore, from time to time, it is probably useful to gather and classify the scattered data concerning this or that class of compounds in order to save time for chemists planning new syntheses or natural products isolations As a continuation of his previous Handbook of Hydroxyacetophenones, R MARTIN now tackles the Hydroxybenzophenones and related aromatic ketones in a new Handbook including circa 1900 molecules and 1500 references up to June 1999 The data concern the syntheses routes or natural origin, physicochemical and spectroscopical characteristics available in the literature and, should the occasion arise a criticism of dubious structures or constants Since hydroxyketones are widely utilized, themselves or as intermediates, in numerous syntheses interesting, among others, pharmaceuticals, dyes, agrochemicals, perfumes and plastic preservatives, this handbook will be of great value for both academic and industrial research chemists The multiple ways of hydroxybenzophenones syntheses herein described will certainly help chemists, as most of these methods can be applied to prepare analogues in aromatic and even in some heterocyclic series The three exhaustive indexes enable the reader to rapidly find a compound and its isomers if previously published or patented and to select the best way for preparation Considering the large amount of information included in this Handbook, I guess it will be entirely successful P Demerseman ACKNOWLEDGEMENTS I wish to express my heartily thanks to Dr Pierre Demerseman who accepted me in his Laboratory at Institut Curie in 1987, and kindly revised my manuscript The foreword of this Handbook was also redacted by Dr Pierre Demerseman I most appreciate this mark of kindness I am also grateful to Dr J.-P Buisson, always so amiable and efficient, whose knowledge of wordprocessing largely contributed to the final page-setting of this work My thanks are also directed to Prof Claude Monneret, Head of the Chemical Department at Institut Curie, who has always been so benevolent to me, and all his collaborators for their warm welcome at each of my visits I thank my son Serge Martin for friendly advice on the english redaction of this book Moreover, Mr Serge Martin was a constant aid to me as regards data processing The author also thanks Prof Jean Paul Guette for all his good advices Various friends who readily accepted to translate foreign publications are also to be acknowledged here, in particular Dr Jean Burkhard who has been of unvaluable help for translating german papers over the last 30 years The diverse abbreviations used in ancient reviews - particularly Chemisches Zentralblatt - had no secrets for him In this connection, thanks are due to Mrs Feiga Weisbuch for her precious assistance as regards rumanian and russian texts, as well as to Miss Marie-Frangoise Liachenko and Dr Daniel Dauzonne I wish to express my thanks to Mrs Mireille Guyonneau, Mrs Elisabeth Matarasso, Mrs Franchise Remy and Mrs Simonne Risse for their keen contribution to my bibliographic research, as well as the Orsay University Library for their helpful kindness towards me for 30 years now I am also grateful to Mrs Colette Ledoux for judicious advice in the field of scientific edition Before closing, I would like to remember my dear departed My affectionate thoughts are turned towards Prof Leon Denivelle who transmitted to me his passion for aromatic organic Chemistry in 1945, and Prof Albeit Kirrmann who accepted me among his students in 1961 and was always so amiable and well-disposed whenever I went to him I cannot mention without emotion Prof Albert Saint-Maixen who largely communicated to me his knowledge on analytical Chemistry I also have a personal thought towards my friends from the industry who left us too soon I am particularly thankful to Drs Henri Barbier, Felix Lepors and Henri Ruelleux (SPCA, Ltd.) who gave me the practical means to carry about my work on aromatic hydroxyketones In this firm, I started my research on the Fries reaction I also wish to acknowledge the late Dr Frangois Krausz who, at that time, made me benefit from his precious advice Robert MARTIN INTRODUCTION Acylphenols are used as starting material for an extremely large number of syntheses in organic chemistry, leading to a wide range of applications For this reason, it seemed interesting to offer a dictionary of Benzoylphenols or Hydroxybenzophenones, since they constitute the most numerous and currently used representatives of this series of compounds Moreover, most syntheses of Hydroxybenzophenones can be extended to their other homologs not described here The dictionary covers over 1,900 Hydroxybenzophenones methodically classified under the official nomenclature of "Methanones" according to the International System (LU.P.A.C.) and the recommendations given in the Chemical Abstracts "Collective Index" (9 CI) since 1972 About 1,500 bibliographic references are compiled in this work Names of periodicals are abbreviated according to the Chemical Abstracts Service Source Index (CA.S.S.I.) Whenever Hydroxybenzophenones can be obtained from plants, sources and corresponding references are given For each compound described, the different protocols of synthesis are presented as well as the main physico-chemical characteristics and references of spectroscopic data Besides, the usual abbreviations are also indicated at the end of this Dictionary For precise and quick research of an Hydroxybenzophenone, you can refer either to the classification by molecular formula (Molecular Formula Index) or to the Chemical Abstracts Registry Numbers table An entry Usual Names Index including the current names of some Hydroxyacetophenones and their precursors is also available Finally, a glance through any chapter of this Dictionary will inform the reader on the diverse ways of synthesizing Hydroxybenzophenones These methods can be used to obtain hitherto unknown analogs in the related series Contents Preface xi Acknowledgements xiii Introduction xv Part I Monoaroylphenols Unsubstituted Hydroxybenzophenones (Class of METHANONES) Monohydroxybenzophenones Dihydroxybenzophenones 2.1 Hydroxy Groups Located on One Ring 2.2 Hydroxy Groups Located on Both Rings Symmetrical Ketones Asymmetric Ketones 8 13 13 15 Trihydroxybenzophenones 3.1 Hydroxy Groups Located on One Ring 3.2 Hydroxy Groups Located on Both Rings 17 17 19 Tetrahydroxybenzophenones 4.1 Hydroxy Groups Located on One Ring 4.2 Hydroxy Groups Located on Both Rings Symmetrical Ketones Asymmetric Ketones 22 22 22 22 24 Pentahydroxybenzophenones 5.1 Hydroxy Groups Located on One Ring 5.2 Hydroxy Groups Located on Both Rings 28 28 28 Hexahydroxybenzophenones Symmetrical Ketones Asymmetric Ketones 32 32 33 This page has been reformatted by Knovel to provide easier navigation vii viii Contents Substituted Hydroxybenzophenones (Class of METHANONES) 35 Monohydroxybenzophenones 1.1 Substituents Located on the Hydroxylated Ring Phenyl(2,3,5-trichloro-6-hydroxyphenyl)methanone to (2Hydroxy-4,5-dimethylphenyl) phenylmethanone (2-Hydroxy-4,6-dimethyIphenyl)phenylmethanone to [2Hydroxy-3,5-bis(3-methyl-2-butenyl)-4,6-bis[[(4methylphenyl)sulfonyl]oxy]phenyl]phenylmethanone 1.2 Substituents Located on the Other Ring 1.3 Substituents Located on Both Rings (2,4-Dichlorophenyl)(2,3,5-trichloro-6-hydroxyphenyl) methanone to (2-Hydroxy-5-methoxyphenyl)(4nitrophenyI)methanone (4-Hydroxy-3-methoxyphenyl)(2-nitrophenyl)methanone to (3,4-Dichlorophenyl)[5-(1,1-dimethylethyl)-2hydroxyphenyl]methanone (2,4-DichIorophenyl)[4-hydroxy-2-methyl-5-(1-methyIethyi) phenyl]methanone to [4-(4-Dodecylphenoxy)-2hydroxyphenyI](4-dodecylphenyl)methanone 35 35 288 Dihydroxybenzophenones 2.1 Hydroxy Groups Located on the Same Ring 2.1.1 Substituents Located on the Hydroxylated Ring 2.1.2 Substituents Located on the Other Ring 2.1.3 Substituents Located on Both Rings 2.2 Hydroxy Groups Located on Both Rings 2.2.1 Substituents Located on One Ring 2.2.2 Substituents Located on Both Rings 339 339 339 365 382 396 396 413 Trihydroxybenzophenones 3.1 Hydroxy Groups Located on the Same Ring 3.1.1 Substituents Located on the Hydroxylated Ring 3.1.2 Substituents Located on the Other Ring 436 436 436 437 This page has been reformatted by Knovel to provide easier navigation 35 80 126 169 169 229 Contents 3.2 ix Hydroxy Groups Located on Both Rings 442 3.2.1 Substituents Located on One Ring 442 3.2.2 Substituents Located on Both Rings 450 Tetrahydroxybenzophenones 4.1 Hydroxy Groups Located on One Ring (Not Described till December 1999) 4.2 Substituents Located on Both Rings 4.2.1 Substituents Located on One Ring 4.2.2 Substituents Located on Both Rings 458 Pentahydroxybenzophenones 5.1 Hydroxy Groups Located on One Ring (Not Described till December 1999) 5.2 Hydroxy Groups Located on Both Rings 5.2.1 Substituents Located on One Ring 5.2.2 Substituents Located on Both Rings 465 458 458 458 463 465 465 465 467 Hexahydroxybenzophenone 468 Polyphenyl Phenyl Methanones (Class of METHANONES) 469 Biphenyl Phenyl Methanones 469 1.1 Monohydroxylated Ketones 469 1.2 Dihydroxylated Ketones 475 Terphenyl Phenyl Methanones 478 Cyclohexyl Phenyl Methanones (Class of METHANONES) 479 Monohydroxylated Ketones 479 Dihydroxylated Ketones 484 Trihydroxylated Ketones 485 Part II Diaroylphenols and Polyaroylphenols Phenols with One Benzoyl Group and One or Several Acetyl Groups (Class of ETHANONES) 487 Monohydroxylated Ketones 487 Dihydroxylated Ketones 489 This page has been reformatted by Knovel to provide easier navigation x Contents Symmetrical Ketones 489 Asymmetric Ketones 489 Trihydroxylated Ketone 491 Tetrahydroxylated Ketone 492 Phenols with Two or Several Benzoyl Groups (Class of METHANONES) 493 Monohydroxylated Ketones 493 Symmetrical Ketones 493 Asymmetric Ketones 496 Di- and Polyhydroxylated Ketones 498 Symmetrical Ketones 498 Asymmetric Ketones 507 Part III Miscellaneous Related Compounds (Class of METHANONES) Diphenyl Derivatives 509 Diphenylmethane Derivatives 511 Diphenylethane Derivative 513 Diphenylpropane Derivatives 514 Diphenyl Oxide Derivatives 514 Diphenyl Sulfoxide Derivatives 516 Diphenyl Sulfone Derivatives 517 Others Acylated Compounds 519 References 521 Indexes Molecular Formula Index 561 Chemical Abstracts Registry Numbers Index 645 Usual Names Index 707 Common Abbreviations 717 This page has been reformatted by Knovel to provide easier navigation 703 Index terms Links [169696-58-6] to [183725-95-3] [169696-58-6] (2,5-Dihydroxyphenyl)[4-(1,1-dimethylethyl)phenyl]methanone [169781-83-3] (4-Fluoro-2-hydroxyphenyl)phenylmethanone 46 [169781-84-4] (2-Chloro-4-fluoro-6-hydroxyphenyl)phenylmethanone 36 [169781-85-5] (4-Chloro-2-hydroxyphenyl)(4-fluorophenyl)methanone 181 [169781-86-6] (4-Chlorophenyl)(4-fluoro-2-hydroxyphenyl)methanone 183 [170630-11-2] (3,5-Dihydroxy-4-methoxyphenyl)(2,3,4trihydroxyphenyl)methanone 381 466 [170744-87-3] (4-Hydroxy-3-iodophenyl)phenylmethanone [170799-04-9] (5-Chloro-2-hydroxy-4-methylphenyl)(2-methylphenyl)methanone 246 [170799-15-2] (5-Ethyl-2-hydroxyphenyl)(2-methylphenyl)methanone 273 [170799-16-3] [2-Hydroxy-5-(1-methylethyl)phenyl](2-methylphenyl)methanone 298 [170799-17-4] (2-Chlorophenyl)(2-hydroxy-4,5-dimethylphenyl)methanone 248 [170799-18-5] (4-Chloro-2-hydroxy-5-methylphenyl)(2-methylphenyl)methanone 245 [172479-19-5] (2-Hydroxy-6-methyl-4-propoxyphenyl)phenylmethanone 104 [172479-20-8] (2-Hydroxy-3-methyl-4-propoxyphenyl)phenylmethanone 104 [172479-21-9] (2-Hydroxy-4-propoxyphenyl)(2-methylphenyl)methanone 299 18 47 [172546-74-6] (3,4-Dihydroxy-5-nitrophenyl)[2-(fluoro- F)phenyl]methanone 386 [174186-21-1] (2,6-Dichlorophenyl)(2-hydroxy-5-methylphenyl)methanone 205 [176547-98-1] (2,5-Dihydroxyphenyl)(2-fluorophenyl)methanone 370 [176548-03-1] (4,4’-Dihydroxy[1,1'-biphenyl]-2,2'-diyl)bis[(3fluorophenyl)methanone 509 (3,5-Dihydroxyphenyl)[4-(phenoxy-3,5-d2)phenyl]methanone 381 [176738-21-9] [176738-22-0] [3-Hydroxy-5-(phenoxy-d5)phenyl][4-(phenoxy-3,5d2)phenyl]methanone 332 [177703-29-6] (3,4-Dihydroxy-2-methoxyphenyl)phenylmethanone 353 [177703-30-9] (2,3-Dihydroxy-4-methoxyphenyl)(3,4,5trihydroxyphenyl)methanone 466 [177703-35-4] [3,4-Bis(acetyloxy)-2-hydroxyphenyl]phenylmethanone 95 [177703-36-5] [2,3-Bis(acetyloxy)-4-hydroxyphenyl]phenylmethanone 95 This page has been reformatted by Knovel to provide easier navigation 704 Index terms Links [179018-47-4] (2-Fluoro-4-hydroxyphenyl)phenylmethanone 45 [179018-48-5] (3,5-Difluoro-4-hydroxyphenyl)phenylmethanone 40 [179018-49-6] (2,5-Difluoro-4-hydroxyphenyl)phenylmethanone 39 [182499-94-1] (3-Hydroxy-4-nitrophenyl)phenylmethanone 48 [182499-95-2] (2-Hydroxy-3-nitrophenyl)phenylmethanone 47 [183013-50-5] (4-Hydroxy-3-propylphenyl)phenylmethanone 91 [183106-12-9] (3,4-Dimethoxyphenyl)(2-hydroxyphenyl)methanone 159 [183106-13-0] (2,5-Dihydroxyphenyl)(2-hydroxyphenyl)methanone 20 [183106-14-1] (2,5-Dimethoxyphenyl)(2-hydroxyphenyl)methanone 159 [183106-15-2] (2-Bromophenyl)(2-hydroxy-4-methoxyphenyl)methanone 211 [183106-19-6] (2-Fluorophenyl)(2-hydroxy-5-methoxyphenyl)methanone 223 [183106-21-0] (2-Chlorophenyl)(2-hydroxy-5-methoxyphenyl)methanone 219 [183106-23-2] (2-Bromophenyl)(2-hydroxy-5-methoxyphenyl)methanone 211 [183106-25-4] (2-Hydroxy-5-methoxyphenyl)(3-methoxyphenyl)methanone 265 [183280-18-4] Cyclohexyl(5-fluoro-2-hydroxyphenyl)methanone 480 [183280-19-5] (3-Fluoro-2-hydroxyphenyl)phenylmethanone 46 [183280-20-8] (3,5-Difluoro-2-hydroxyphenyl)phenylmethanone 40 [183280-21-9] (5-Fluoro-2-hydroxyphenyl)[4-(trifluoromethyl)phenyl]methanone [183589-15-3] (3-Ethynyl-4-hydroxyphenyl)phenylmethanone [183589-17-5] [4-Hydroxy-3-(phenylethynyl)phenyl]phenylmethanone 115 [183589-20-0] [3-(1-Hexynyl)-4-hydroxyphenyl]phenylmethanone 109 [183724-10-9] (2,6-Dichlorophenyl)(5-hydroxy-4-methoxy-2- 194 72 methylphenyl)methanone 243 [183724-89-2] (2,6-Dichlorophenyl)(4-hydroxy-2,3,6-trimethylphenyl)methanone 268 [183725-20-4] (2,6-Dichlorophenyl)(2-hydroxy-4,5-dimethoxyphenyl)methanone 243 [183725-80-6] (2,6-Dichiorophenyl)(2,3-dihydroxy-4-methoxy-6methylphenyl)methanone 391 [183725-86-2] (2,6-Dichlorophenyl)(4-hydroxy-2-methyl-5-nitrophenyl)methanone 195 [183725-95-3] (2-Hydroxy-3,4-dimethoxy-6-methyl)(2,3,5,6tetramethylphenyl)methanone 325 This page has been reformatted by Knovel to provide easier navigation 705 Index terms Links [183726-43-4] to [205319-41-1] [183726-43-4] (2,6-Dichlorophenyl)(2-hydroxy-3,4-dimethoxy-6methylphenyl)methanone 268 (2,6-Dichlorophenyl)(2-hydroxy-4-methoxy-6methylphenyl)methanone 242 [188347-38-8] (2,4-Dihydroxyphenyl)(2,4,6-trinitrophenyl)methanone 365 [190522-97-5] (4-Hydroxy-3-methoxyphenyl)(2-nitrophenyl)methanone 229 [190522-98-6] (4-Hydroxy-3-methoxy-5-nitrophenyl)(2-nitrophenyl)methanone 209 [190523-00-3] (3,4-Dihydroxy-5-nitrophenyl)(2-nitrophenyl)methanone 387 [190585-63-8] [4-Hydroxy-3-nitro-5-(phenylmethoxy)phenyl](2nitrophenyl)methanone 324 [3-(Cyclohexyloxy)-4-hydroxy-5-nitrophenyl](2nitrophenyl)methanone 317 [183726-73-0] [190585-64-9] [190585-65-0] [3-[(2,6-Dichlorophenyl)methoxy]-4-hydroxy-5-nitrophenyl](2-nitrophenyl)methanone [190585-66-1] 323 18 [2-(Fluoro- F)phenyl](4-hydroxy-3-methoxy-5nitrophenyl)methanone 208 [190728-23-5] (2,6-Dihydroxy-4-methylphenyl)(4-hydroxyphenyl)methanone 444 [190728-32-6] (4-Hydroxyphenyl)[2-(trifluoromethyl)phenyl]methanone 145 [190728-33-7] (4-Butylphenyl)(4-hydroxyphenyl)methanone 164 [190728-34-8] (3-Fluorophenyl)(4-hydroxyphenyl)methanone 137 [192437-36-8] (4-Bromophenyl)(2,5-difluoro-4-hydroxyphenyl)methanone 174 [192443-11-1] (4-Bromo-2-fluorophenyl)(4-hydroxyphenyl)methanone 126 [192443-53-1] (4-Bromophenyl)[2-(dibromomethyl)-4-hydroxyphenyl]methanone 194 [194290-73-8] (2-Fluoro-5-hydroxyphenyl)(3-nitrophenyl)methanone 188 [194290-75-0] (2-Fluoro-4-hydroxyphenyl)(3-nitrophenyl)methanone 188 [194548-68-0] (2-Hydroxyphenyl)(2-phenoxyphenyl)methanone 166 [197169-08-7] (2-Hydroxy-4,6-dimethoxy-1,3-phenylene)bis[phenylmethanone 494 [197355-26-3] (2-Hydroxy-3,4,5-trimethoxyphenyl)(2,3,4trimethoxyphenyl)methanone 322 [198879-06-0] Phenyl(2,3,4,6-tetrahydroxyphenyl)methanone This page has been reformatted by Knovel to provide easier navigation 22 706 Index terms [199735-29-0] Links (2-Hydroxy-3-methoxy-5-methylphenyl)(4-hydroxy-3methoxyphenyl)methanone 428 (4-Hydroxy-3,5-dimethoxyphenyl)(5-hydroxy-4-methoxy-2methylphenyl)methanone 431 [200420-24-2] (1-Hydroxycyclohexyl)(4-hydroxyphenyl)methanone 485 [203060-34-8] (4-Hydroxy-2-methylphenyl)(4-nitrophenyl)methanone 227 [203060-35-9] (3,4-Dihydroxyphenyl)(4-nitrophenyl)methanone 372 [203060-36-0] (3,4-Dihydroxyphenyl)(3-nitrophenyl)methanone 372 [203448-32-2] (3-Hydroxy-4-methoxyphenyl)(3,4,5-trimethoxyphenyl)methanone 304 [203786-32-7] [3-(1,1-Dimethylethyl)-4-hydroxyphenyl](2,4dimethylphenyl)methanone 319 (2-Hydroxyphenyl)[2-(trifluoromethyl)phenyl]methanone 144 [199735-38-1] [205319-41-1] This page has been reformatted by Knovel to provide easier navigation Usual Names Index Index terms Links A Adlone see to Exifone 33 Alizarine yellow A 2,3,4-Trihydroxybenzophenone 17 Anisaldehyde (o, m or p) (2, or4)-Methoxybenzaldehyde 218 300 377 Anisic acid (o, m or p) (2, or 4)-Methoxybenzoic acid 153 392 261 440 276 376 126 130 132 136 263 149 500 151 155 Anisoyl chloride (o, m or p) (2, or 4)-Methoxybenzoyl chloride 128 149 218 284 405 132 155 261 305 409 20 136 162 264 376 441 27 138 166 279 396 507 Anthranil 2,1-Benzisoxazole and also Benzopseudoxazole 142 Anthrone 9(10H)-Anthracenone 488 Anisole methoxybenzene Aurin 4-[Bis(4-hydroxyphenyl)methylene]-2,5-cyclohexadien-1one and also p-Rosolic acid 496 14 B Baishouwubenzophenone 3-Acetyl-2,3',6,6'-tetrahydroxy-2'methylbenzophenone Benzaurine Hydroxyfuchsone 492 70 This page has been reformatted by Knovel to provide easier navigation 707 708 Index terms Links Benzenyl chloride Benzenyl trichloride or(Trichloromethyl)benzene Benzhydrol Benzohydrol or diphenylcarbinol 2,1-Benzisoxazole Anthranil Benzofuran Coumarone Benzoresorcinol 2,4-Dihydroxybenzophenone 122 126 371 51 142 229 11 38 42 47 74 90 110 255 299 376 54 78 97 153 260 310 389 64 82 101 220 262 340 480 67 84 106 244 274 346 496 Benzotrichloride (Trichloromethyl)benzene 36 65 106 119 493 42 77 110 344 10 44 100 114 355 17 62 102 117 361 2-Benzoxazolinone 2-Hydroxybenzoxazole 52 72 192 230 266 401 407 Bisphenol A 4,4'-(1-Methylethylidene)bisphenol 514 C Carvacrol 2-Methyl-5-isopropylphenol Cearoin 2,5-Dihydroxy-4-methoxybenzophenone Cellosolve 2-Ethoxyethanol 66 102 352 10 120 Cotogenin 3',4'-Dihydroxy-2,4,6-trimethoxybenzophenone 380 Cotoin 2,6-Dihydroxy-4-methoxybenzophenone 348 Coumarin 2H-1-Benzopymn-2-one 11 354 21 367 Creosol 2-Methoxy-4-methylphenol 64 85 This page has been reformatted by Knovel to provide easier navigation 86 344 709 Index terms Cresol (o, m or p) (2, or 4)-Methylphenol Links 61 65 197 203 210 230 355 481 214 237 402 493 216 246 419 502 222 261 471 o-Cresotic acid 2-Hydroxy-3-methylbenzoic acid or 3methylsalicylic acid 444 460 m-Cresotic acid 2-Hydroxy-4-methylbenzoic acid 444 460 p-Cresyl anthranilate 4-Methylphenyl 2-aminobenzoate 233 214 217 Cumene (1-Methylethyl)benzene 81 Cyasorb UV-9 2-Hydroxy-4-methoxybenzophenone and Oxybenzone 67 161 Cyasorb UV-24 2,2'-Dihydroxy-4-methoxybenzophenone or Dioxybenzone Cyasorb UV-531 2-Hydroxy-4-(octyloxy)benzophenone 405 111 D Dalbergin 6-Hydroxy-7-methoxy-4-phenylcoumarin 86 Dastib 242 2-Hydroxy-4-(2-ethylhexyloxy)benzophenone 118 Dehydrogriseofulvin 7-Chloro-2',4,6-trimethoxy-6'methylspiro[benzofuran-2(3H),1'-[2,5]cyclo-hexadiene-3,4'dione 429 Diethylene glycol 2,2'-Oxybisethanol 117 Diglycol Diethylene glycol 475 Dioxocin 2H,6H-1,5-Dioxocin [292-95-5] Dioxybenzone 2,2'-Dihydroxy-4-methoxybenzophenone 63 475 204 405 Disyringylmethane 4,4'-Dihydroxy-3,3',5,5'tetramethoxydiphenylmethane 421 This page has been reformatted by Knovel to provide easier navigation 710 Index terms Links E Epichlorohydrin 1-Chloro-2,3-epoxypropane 89 Ethylcellosolve Cellosolve or 2-Ethoxyethanol 10 Everninic acid 2-Hydroxy-4-methoxy-6-methylbenzoic acid Exifone 2,3,3',4,4',5'-Hexahydroxybenzophenone 452 33 464 257 48 132 31 33 F 9-Fluorenone 9-Oxofluorene Fluoresin chloride 2-(3,6-Dihydroxy-9H-xanthen-9-yl)-benzoic acid chloride Fuchsone (4-Diphenylmethylene-2,5-cyclohexadien-1-one) 22 70 G Gallacetophenone 2',3',4'-Trihydroxyacetophenone 17 Gallic acid 3,4,5-Trihydroxybenzoic acid 28 Gentisein 1,3,7-Trihydroxyxanthone 27 Gentisic acid 2,5-Dihydroxybenzoic acid 23 Glyme 1,2-Dimethoxyethane 116 Griseofulvin 7-Chloro-2',4,6-trimethoxy-6'methylspiro[benzofuran-2(3H),1'-[2]cyclohexene]-3,4'-dione 466 Griseophenone A 3-Chloro-2,4'-dihydroxy-2',4,6-tnmethoxy-6'methylbenzophenone 429 Griseophenone B 3-Chloro-2,4',6-trihydroxy-2',4-dimethoxy-6'methylbenzophenone Griseophenone C 2,4',6-Trihydroxy-2',4-dimethoxy-6'methylbenzophenone Guaiacol 2-Methoxyphenol 454 456 312 456 70 This page has been reformatted by Knovel to provide easier navigation 148 711 Index terms Links H Hydrocotoin 2-Hydroxy-4,6-dimethoxybenzophenone Hydroquinone 1,4-Benzenediol Hydroxyhydroquinone 1,2,4-Benzenetriol 72 75 86 494 11 228 301 366 395 20 264 314 369 508 23 281 320 378 68 289 335 381 30 302 312 438 I 1,2-Indanedione α,β-Dioxohydrindene 496 Iriflophenone 2,4,4',6-Tetrahydroxybenzophenone 28 Isocotoin 2,4-Dihydroxy-6-methoxybenzophenone 360 Isoeugenol 2-Methoxy-4-propenylphenol 420 b-Isoeuxanthone 2,7-Dihydroxyxanthone 23 Isophthalic acid 1,3-Benzenedicarboxylic acid 364 500 L Light Absorber HCB 5-Chloro-2-hydroxybenzophenone 44 M Maclurin 2,3',4,4',6-Pentahydroxybenzophenone 31 467 Melanoxoin 2,3',5-Trihydroxy-4,4'-dimethoxybenzophenone 451 Mesitoyl chloride 2,4,6-Trimethylbenzoyl chloride 162 308 Mesitylene 1,3,5-Trimethylbenzene 162 374 117 120 1-Methylpyrrolidone 1-Methyl-2-pyrrolidinone or NMethylpyrrolidone Mexenone 2-Hydroxy-4-methoxy-4'-methylbenzophenone Morin 2-(2,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-1benzopyran-4-one 260 31 This page has been reformatted by Knovel to provide easier navigation 712 Index terms Links N Nitrazepam 1,3-Dihydro-7-nitro-5-phenyl-2H-1,4-benzodiazepin2-one Nizofenone (2-Chlorophenyl)[2-[2-[(diethylamino)methyl]-1Himidazol-1-yl]-5-nitrophenyl]methanone 51 185 O Octabenzone 2-Hydroxy-4-(octyloxy)benzophenone 111 Orcinol 5-Methyl-1,3-benzenediol 349 452 465 468 Orsellinic acid 2,4-Dihydroxy-6-methylbenzoic acid 463 o-Orsellinic acid 2,4-Dihydroxy-6-methylbenzoic acid or 4,6Dihydroxy-o-toluic acid 466 γ-Orsellinic acid 2,6-Dihydroxy-4-methylbenzoic acid 452 455 463 p-Orsellinic acid 2,6-Dihydroxy-4-methylbenzoic acid or 2,6Dihydroxy-p-toluic acid Oxybenzone 2-Hydroxy-4-methoxybenzophenone 54 58 67 488 490 129 131 145 149 278 18 352 361 Phloroglucinol 1,3,5-Benzenetriol 18 163 380 445 485 26 284 394 459 491 31 303 438 461 504 86 352 441 465 Prenyl bromide 4-Bromo-2-methyl-2-butene 105 413 123 437 330 358 P Paeonol 2'-Hydroxy-4 '-methoxyacetophenone Phenetole Ethoxybenzene Phenstatin 3'-Hydroxy-3,4,4',5-tetramethoxybenzophenone 304 Phenyl mesitoate Phenyl 2,4,6-trimethylbenzoate 162 Phlorobenzophenone 2,4,6-Trihydroxybenzophenone This page has been reformatted by Knovel to provide easier navigation 140 713 Index terms Links Protocatechuic acid 3,4-Dihydroxybenzoic acid 25 Protocatechuonitrile 3,4-Dihydroxybenzonitrile 31 Pyrocatechol 1,2-Benzenediol 28 Pyrogallol 1,2,3-Benzenetriol Pyruvic acid 2-Oxopropanoic acid 31 12 31 21 24 17 26 29 32 85 303 458 163 315 460 283 409 483 300 438 77 81 90 415 Q Quinbenzophenone 2,5-Dihydroxybenzophenone 11 Quinol 1,4-Benzenediol 113 Quinoline Benzo[b]pyridine 70 471 R Resacetophenone 2',4'-Dihydroxyacetophenone 489 Resbenzophenone 2,4-Dihydroxybenzophenone 70 73 82 87 103 117 345 363 89 107 120 349 383 92 111 340 358 490 94 113 342 360 515 67 219 279 365 442 485 508 19 113 223 310 374 461 498 22 118 237 344 376 472 503 28 158 264 347 419 476 506 Resorcinol 1,3-Benzenediol This page has been reformatted by Knovel to provide easier navigation 714 Index terms β-Resorcylic acid 2,4-Dihydroxybenzoic acid Links 10 20 447 450 Rosaniline Fuchsine 14 p-Rosolic acid Aurin 14 23 29 S Salicylaldehyde 2-Hydroxybenzaldehyde Salicylic acid 2-Hydroxybenzoic acid Salicylic acid chloride 2-Hydroxybenzoyl chloride Salicyloyl chloride 2-Hydroxybenzoyl chloride 135 151 377 14 76 19 154 26 405 40 442 247 161 Salicylonitrile 2-Hydroxybenzonitrile 26 Salol Phenyl salicylate 13 15 Scleroin 2,5-Dihydroxy-3,4-dimethoxybenzophenone 356 Styrene Ethenylbenzene 115 124 Sulfolane Tetrahydrothiophene 1,1-dioxide 23 29 Sumisorb 110 2-Hydroxy-4-methoxybenzophenone 67 520 T Tannic acid Tannin or Gallotannin 33 Terephthalic acid 1,4-Benzenedicarboxylic acid 501 Terephthalonitrile 1,4-Dicyanobenzene 500 Terephthaloyl chloride 1,4-Benzenecarbonyl chloride 501 505 Thymol 5-Methyl-2-isopropylphenol 65 165 79 288 p-Thymol 3-Methyl-4-isopropylphenol 102 166 Tolualdehyde (o, m or p) (2, or 4)-Methylbenzaldehyde 375 Toluic acid (o, m or p) (2, or 4)-Methylbenzoic acid 149 462 Toluoyl chloride (o, m or p) (2, or 4)-Methylbenzoyl chloride 148 101 107 374 465 390 440 212 256 278 308 This page has been reformatted by Knovel to provide easier navigation 715 Index terms Tolyl benzoate (o, m or p) (2, or 4)-Methylphenyl benzoate Links 61 225 133 515 136 155 Umbelliferone 7-Hydroxycoumarin 11 356 375 UV 2-Hydroxy-5-methylbenzophenone 68 Triflic acid Trifluoromethanesulfonic acid 470 U UV 12 2,2'-Dihydroxy-4,4'-dimethoxybenzophenone 419 Uvinul D-49 2,2'-Dihydroxy-4,4'-dimethoxybenzophenone 419 Uvinul D-50 2,2',4,4'-Tetrahydroxybenzophenone Uvinul 490 2,2'-Dihydroxy-4,4'-dimethoxybenzophenone Uvinul 400 2,4-Dihydroxybenzophenone 22 419 Uvinul 3049 2,2 '-Dihydroxy-4,4'-dimethoxybenzophenone 419 Uvistat 247 2-Hydroxy-4-n-heptyloxybenzophenone 115 V Vanilionitrile 4-Hydroxy-3-methoxybenzonitrile 447 461 Veratric acid 3,4-Dimethoxybenzoic acid 159 380 24 369 Veratrole 2,2-Dimethoxybenzene Veratronitrile 3,4-Dimethoxybenzonitrile 304 Veratroyl chloride 3,4-Dimethoxybenzoyl chloride 283 Vismiaphenone A 2,4-Dihydroxy-6-methoxy-3,5diprenylbenzophenone 364 302 380 30 466 13 417 489 19 426 154 299 79 407 X Xanthone 9H-Xanthen-9-one Xylene (o, m or p) (1,2-, 1,3- or 1,4-)Dimethylbenzene Xylenol Dimethylphenol (6 isomers) This page has been reformatted by Knovel to provide easier navigation 23 451 COMMON ABBREVIATIONS Common abbreviations used in the dictionary for organic chemistry A Angstrom units b.p Boiling point (for example, b.p.o.i 100° means boils at 100° if the pressure is 0.1 mm Hg) (d) Decomposition 20° 20 degrees Celsius d Density (for example, d20 specific gravity at 200C referred to water at 4°C) DDQ 2,3-Dichloro-5,6-dicy anobenzoquinone EPR Electron paramagnetic resonance HMPT Hexamethylphosphoric Triamide 13 C NMR (E) Nuclear magnetic resonance relative to carbon 13 Geometric stereodescriptor used for compounds having achiral elements resulting from double bonds where the groups of highest priority are on the opposite sides of the vertical reference plane 19 Nuclear magnetic resonance relative to fluorine 19 F NMR GC Gas chromatography GC-MS Gas chromatography-mass spectrometry GLC Gas-liquid chromatography h Hour Nuclear magnetic resonance relative to proton H NMR HPLC High pressure liquid chromatography IR Infrared (spectra) iso- Aliphatic hydrocarbon having two methyl groups on the terminal carbon atom of the chain (for example, isoamyl (CH3)2CH-CH2-CH2-) LDA lithium diisopropylamide m- Meta- M Molar (concentration) Minute mol Molecule mol.wt Molecular weight m.p Melting point MS Mass spectra n- Normal, as n-butyl N Normal (equivalents per liter, as applied to concentration) NA Not available N.B.: Notabene no 20 Index of refraction (no20 for 200C and sodium light) o- Ortho- p- Para- Pa pascal Pd/C Palladium on charcoal pATa L o g of the reciprocal of the dissociation constant, 1/log K& Rh/C Rhodium on charcoal r.t Room temperature Sadtler Sadtler Research Laboratories, Philadelphia (USA) SDS Sodium dodecyl sulfate sec- Secondary SM Starting material tert- Tertiary- TFAA Trifluoroacetic anhydride TFMS Trifluoromethanesulfonic acid TLC Thin layer chromatography UV Ultraviolet (spectra) Vol Volume (Z) Opposite of (E) ... handbook will be of great value for both academic and industrial research chemists The multiple ways of hydroxybenzophenones syntheses herein described will certainly help chemists, as most of. .. extremely large number of syntheses in organic chemistry, leading to a wide range of applications For this reason, it seemed interesting to offer a dictionary of Benzoylphenols or Hydroxybenzophenones, ... representatives of this series of compounds Moreover, most syntheses of Hydroxybenzophenones can be extended to their other homologs not described here The dictionary covers over 1,900 Hydroxybenzophenones