The Additional Ring Is Benzene Patents (Class 568/744)
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Patent number: 4599464Abstract: Novel compositions useful as antioxidants are formed by the reaction of resorcinol with an alkenylbenzene.Type: GrantFiled: October 17, 1985Date of Patent: July 8, 1986Assignee: Koppers Company, Inc.Inventor: Hans Dressler
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Patent number: 4594460Abstract: Substituted phenols of formula ##STR1## in which R.sub.1 is in an ortho or para position relative to the phenol function and denotes ##STR2## R.sub.2 denotes an acyclic radical optionally substituted by alkyl, hydroxy, alkoxycarbonyl, cyano or formyl, or a phenyl or naphthyl radical, and R denotes hydrogen or 1 to 4 substituents chosen from halogen, OH optionally in the form of ether or ester, alkyl, NO.sub.2, CHO optionally in the form of acetal, CH.sub.3 CO--, C.sub.6 H.sub.5 CO--, NH.sub.2, alkylamino, dialkylamino or alkoxycarbonyl, it being understood that 2 symbols R may form with the phenyl nucleus a condensed aromatic ring, which comprises reacting a butadiene of formula ##STR3## with a phenol for formula ##STR4## in water in the presence of a rhodium-based catalyst, a water-soluble phosphine and optionally an inorganic or organic base. The products of formula (I) are intermediates for the synthesis of vitamin E, antioxidants, perfumes or insecticides.Type: GrantFiled: March 19, 1985Date of Patent: June 10, 1986Assignee: Rhone-Poulenc SanteInventors: Gerard Mignani, Didier Morel
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Patent number: 4590301Abstract: Compounds of the general formula ##STR1## wherein n, R.sub.1, R.sub.2 and X are defined herein, are effective inhibitors of polymerization of vinylic monomers, particularly acrylic monomers. The inhibitors are easily, efficiently, and thoroughly removed from solution with the monomer by contact with charcoal.Type: GrantFiled: October 24, 1984Date of Patent: May 20, 1986Assignee: Barnes-Hind, Inc.Inventors: Drahoslav Lim, Peter C. Morris
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Patent number: 4532367Abstract: A method is provided for the production of antimicrobially effective phenol derivatives according to general Formula I in which R.sub.1 is bromine or chlorine, R.sub.2 is methyl or ethyl, R.sub.3 is hydrogen or sodium, potassium, ammonium or by alkyl with up to 10 C-atoms substituted ammonium, magnesium, calcium, barium, aluminum, tin, bismuth, copper, zinc, R.sub.4 and R.sub.5 are independently hydrogen, alkyl or alkoxy with up to 5 C-atoms, bromine or chlorine. The compounds are obtained by benzylation of 6-halogen- or 4-halogen-2-alkylphenol, halogenation of 2-alkyl-4-benzylphenol or -6-benzylphenol, or by alkylation of 6-halogen-4-benzylphenol or of 4-halogen-6-benzylphenol and if necessary through reaction of the product with hydroxide, alcoholate, carbonate or hydrogen carbonate of the above-mentioned metals. Water or lipid soluble effective substances are obtained which display a broad antimicrobial activity spectrum.Type: GrantFiled: August 30, 1982Date of Patent: July 30, 1985Assignee: VEB JenapharmInventors: Herbert Teubner, Axel Kramer, Wolfgang Weuffen, Eberhard Schrotter, Gerhard Grubel
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Patent number: 4514577Abstract: Phenols having an unsubstituted ortho-position are benzylated by reaction with a benzyl alcohol in contact with an activated alumina catalyst especially gamma alumina at a temperature sufficient to maintain the reactants in the vapor phase.Type: GrantFiled: October 15, 1982Date of Patent: April 30, 1985Assignee: Ethyl CorporationInventors: Allen H. Filbey, Henry G. Braxton, Jr., Bernard R. Meltsner
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Patent number: 4510338Abstract: The invention relates to new resorcin derivatives of the formula (I) ##STR1## wherein R.sub.1 and R.sub.2 independently represent hydrogen, halogen, trihalomethyl, alkyl having from one to 3 carbon atoms or alkoxy having from one to 3 carbon atoms.According to another aspect of the invention there are provided processes for the preparation of these compounds.The compounds of the formula (I) are pharmacologically active. In particular, they are suitable for the treatment of acute ethanolic intoxication. Pharmaceutical compositions containing them as active ingredient are also within the scope of the invention.Type: GrantFiled: December 27, 1983Date of Patent: April 9, 1985Assignee: Richter Gedeon Vegyeszeti Gyar Rt.Inventors: Edit Toth, Jozsef Torley, Gyorgy Fekete, Laszlo Szporny, Laszlo Vereczkey, Eva Palosi, Imre Klebovich, Pal Vittay, Sandor Gorog, Istvan Hajdu
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4-Hydroxy-benzhydrols, process for their preparation and pharmaceutical compositions containing them
Patent number: 4508926Abstract: The invention relates to new 4-hydroxy-benzhydrols of the formula (I) ##STR1## wherein R.sub.1 and R.sub.2 independently represent hydrogen, halogen, trihalomethyl, alkyl having from one to 4 carbon atoms or alkoxy having from one to 4 carbon atoms, with the proviso that if R.sub.1 is hydrogen, R.sub.2 is other than hydrogen or a 3-trifluoromethyl group, or if R.sub.1 is a 2-methyl group, R.sub.2 is other than a 5-methyl group.According to another aspect of the invention there are provided processes for the preparation of these compounds.The compounds of the formula (I) are pharmacologically active. In particular, they are suitable for the treatment of acute ethanolic intoxication. Pharmaceutical compositions containing them as active ingredients are also within the scope of the invention.Type: GrantFiled: December 27, 1983Date of Patent: April 2, 1985Assignee: Richter Gedeon Vegyeszeti Gyar Rt.Inventors: Edit Toth, Jozsef Torley, Gyorgy Fekete, Laszlo Szporny, Laszlo Vereczkey, Eva Palosi, Imre Klebovich, Pal Vittay, Sandor Gorog, Istvan Hajdu -
Patent number: 4506103Abstract: o-Benzylphenol is prepared by reacting phenol with dibenzyl ether in the presence of .gamma.-aluminum oxide as a condensation agent.o-Benzylphenol is used, inter alia, as such or, after chlorination, in the form of chlorobenzylphenols, as a microbicidal agent.Type: GrantFiled: September 6, 1983Date of Patent: March 19, 1985Assignee: Bayer AktiengesellschaftInventors: Heinz-Peter Hemmerich, Werner Schulte-Huermann, Heinz Dohm
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Patent number: 4473713Abstract: At least one of the other functions comprising an aryl-aliphatic ether, e.g., veratrol, is catalytically hydrolyzed with water, e.g., to guaiacol, in the presence of a catalytically effective amount of a salt of a carboxylic acid.Type: GrantFiled: September 27, 1982Date of Patent: September 25, 1984Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Serge Ratton
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Patent number: 4410739Abstract: Meta-chlorophenols useful as intermediates in various organic syntheses are prepared by selectively catalytically hydrodechlorinating a polychlorophenol in liquid organic phase and in the presence of a nobel metal catalyst and a Lewis acid, said polychlorophenol bearing chlorine substituents in both the meta- and ortho- and/or para-positions.Type: GrantFiled: December 21, 1981Date of Patent: October 18, 1983Assignee: Rhone-Poulenc IndustriesInventor: Georges Cordier
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Patent number: 4398047Abstract: 2-Substituted-4,6-di-t-butylresorcinol represented by the general formula: ##STR1## wherein R represents a straight or branched alkyl group having 1 to 20 carbon atoms, a straight or branched alkenyl group having 2 to 20 carbon atoms and at least one double bond, or an aralkyl group, wherein no tertiary carbon atom of R is directly bonded to the benzene nucleus, is prepared by allowing 4,6-di-t-butylresorcinol to react with a halogen compound represented by the general formula:RXwherein R has the same meaning as defined above, and X represents a halogen atom, excluding the X bonded to a tertiary carbon of R, in an aqueous alkali solution. By further debutylization of the 2-substituted-4,6-t-butylresorcinol, 2-substituted resorcinol represented by the general formula: ##STR2## wherein R has the same meaning as defined above, but the tertiary carbon of R is free from direct bonding to the benzene nucleus, is prepared.Type: GrantFiled: February 23, 1982Date of Patent: August 9, 1983Assignee: Sumitomo Chemical Company, LimitedInventors: Yukihisa Takisawa, Shinichi Hasegawa
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Patent number: 4391827Abstract: Cycloalkanones, cycloalkanols and unsaturated analogs thereof, each of which has at the 3-position a 2-hydroxy-4-substituted phenyl group wherein the 4-position substituent is alkyl which can have an oxygen atom as part of the chain, or aralkyl which can have an oxygen atom as part of the alkyl chain, their use for pharmacological and medicinal purposes, intermediates therefor and processes for their preparation.Type: GrantFiled: July 27, 1981Date of Patent: July 5, 1983Assignee: Pfizer Inc.Inventors: Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
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Patent number: 4390735Abstract: A process for the preparation of a p-allylphenol of the formula I, which comprises reacting a phenol of the formula II with an allyl halide of the formula III ##STR1## in which the symbols R.sub.1 to R.sub.6 and X are as defined in the description, in the presence of a base and a phase transfer catalyst.p-Allylphenols are valuable intermediates and lubricant additives.Type: GrantFiled: October 13, 1981Date of Patent: June 28, 1983Assignee: Ciba-Geigy CorporationInventor: Siegfried Rosenberger
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Patent number: 4366330Abstract: An intermediate useful in the production of liquid crystal esters has a molecular structure ##STR1## in which of the groups R' and R" one is fluorine and the other is hydrogen, and in which R is an alkyl group having more than one carbon atom, an aryl substituted alkyl group or a cyclohexyl substituted alkyl group.These compounds may be prepared from the corresponding alkoxy compounds ##STR2## where R'" is a protective alkyl group such as methyl. These compounds may be used in the production of liquid crystal esters by a conventional esterification with carboxylic acids, or acid derivative, eg chloride, eg containing the radical ##STR3## where X is an alkyl group and ##STR4## is a benzene or cyclohexane ring.Type: GrantFiled: September 30, 1980Date of Patent: December 28, 1982Assignees: BCH Chemicals Limited, The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventors: George W. Gray, David Lacey, John A. Jenner, Martin G. Pellatt
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Patent number: 4357344Abstract: Certain polybutylbenzylphenols and benzyl-3,4-methylenedioxybenzenes are useful for insect control especially as insect chemosterilants and oviposition inhibitors. The benzyl-3,4-methylenedioxybenzenes also find utility as growth inhibitors for mosquito larvae.Type: GrantFiled: March 29, 1979Date of Patent: November 2, 1982Assignee: The United States of America as represented by the Secretary of AgricultureInventor: Leonard Jurd
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Patent number: 4342777Abstract: Certain polybutylbenzylphenols and benzyl-3,4-methylenedioxybenzenes are useful for insect control especially as insect chemosterilants and oviposition inhibitors. The benzyl-3,4-methylenedioxybenzenes also find utility as growth inhibitors for mosquito larvae.Type: GrantFiled: November 5, 1981Date of Patent: August 3, 1982Assignee: The United States of America as represented by the Secretary of AgricultureInventor: Leonard Jurd
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Patent number: 4320235Abstract: 1-(Aralkyl)-2-naphthols are prepared by reacting a 2-naphthol with a styrene in the presence of a carboxylic acid.The 1-(aralkyl)-2-naphthols obtainable by the process according to the invention are valuable starting materials for the preparation of dyes, pest control agents, drugs, ointments, emulsifiers, dispersants, stabilizers, hydraulic fluids, plasticizers, corrosion inhibitors, disinfectants, crop protection agents and scents.Type: GrantFiled: November 21, 1980Date of Patent: March 16, 1982Assignee: BASF AktiengesellschaftInventors: Franz Merger, Gerhard Nestler
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Patent number: 4316996Abstract: Detrimental color change of phenolic antioxidants during production, storage and use in rubbers is inhibited by adding during the synthesis of the phenolic antioxidant a disubstituted hydroxylamine to the catalyst neutralization solution and a substituted oxime together with a disubstituted hydroxylamine to the reaction mixture prior to filtration.Type: GrantFiled: November 17, 1980Date of Patent: February 23, 1982Assignee: The Goodyear Tire & Rubber CompanyInventors: Jacques H. Collonge, Hans Widmer
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Patent number: 4284830Abstract: Monohalogenated hydrocarbyl substituted phenols can be produced by reacting hydrocarbyl substituted phenols with a halogen carrying out the reaction in a diluent such as benzene, alkyl substituted benzenes, and halosubstituted hydrocarbons of 1-3 carbon atoms.Type: GrantFiled: February 1, 1980Date of Patent: August 18, 1981Assignee: Phillips Petroleum Co.Inventors: Ronald D. Knudsen, Darryl R. Fahey
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Patent number: 4275071Abstract: Imidazole derivatives of the formula I and pharmaceutically acceptable acid addition salts thereof are provided: ##STR1## In the formula, R.sub.4 1- or 2-naphthyl, optionally substituted with Cl, Br, or I; 1,2,3,4-tetrahydro-6-naphthyl; 3-duryl, optionally 6-substituted by Cl, Br, I, NO.sub.2, CH.sub.3 or benzyl; mesityl, phenyl 2-, 3- or 4-substituted by OH, NH.sub.2, NO.sub.2, CH.sub.3 CONH, phenyl, phenoxy, cyclohexyl, phenylthio, benzylthio, C.sub.1 -C.sub.6 alkyl or C.sub.1 C.sub.6 alkylthio; 4-bibenzylyl; 3,4-dihydroxyphenyl,n=0, 1 or 2 and(a) R=H, alkyl having 1 to 6 carbon atoms or phenyl R.sub.1 =H, alkyl having 1 to 6 carbon atoms or phenyl one of R.sub.2 and R.sub.3 =H the other of R.sub.2 and R.sub.3 =H, OH, benzoyloxy, C.sub.2 -C.sub.7 alkanoyloxy, N-(C.sub.1 -C.sub.6 alkyl)-carbamoyloxy, N,N-[di-(C.sub.1 C.sub.6)alkyl]-carbamoyloxy, but if R.sub.2 =R.sub.3 =H then R=R.sub.1 =H, or(b) R=H, C.sub.1 -C.sub.6 alkyl, phenyl R.sub.1 =H, C.sub.1 -C.sub.6 alkyl, phenyl R.sub.2 +R.sub.Type: GrantFiled: July 10, 1979Date of Patent: June 23, 1981Assignee: Recordati S.A.Inventors: Dante Nardi, Alberto Tajano, Maria J. Magistretti
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Patent number: 4212762Abstract: Novel mesomorphic substances, constituting, in certain temperature ranges, nematic or smectic liquid crystals which are compounds of the formula: ##STR1## wherein R.sub.1 is an alkyl or alkoxy group containing 1 to 10 atoms of carbon;R.sub.2 is Br, CN or an alkyl (or an alkoxy) group containing 1 to 10 atoms of carbon.Type: GrantFiled: November 21, 1978Date of Patent: July 15, 1980Assignee: Thomson-CSFInventors: Jean-Claude Dubois, Huu Tinh Nguyen, Annie Zann
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Patent number: 4202199Abstract: Alkylphenol compounds are manufactured by continuous reaction of phenolic compounds with olefins in the presence of a pulverulent polystyrenesulfonic acid exchanger suspended in the reaction mixture. The products are starting materials for the manufacture of dyes, pesticides, pharmaceuticals, emulsifiers, dispersing agents, stabilizers, antioxidants, plasticizers, corrosion inhibitors, disinfectants, seed dressings, aging inhibitors, crop protection agents and scents.Type: GrantFiled: October 6, 1977Date of Patent: May 13, 1980Assignee: BASF AktiengesellschaftInventors: Franz Merger, Gerhard Nestler
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Patent number: 4201878Abstract: Bisphenols substantially free of by-products, are produced rapidly by reacting a phenol and a compound of the formulae: ##STR1## wherein R and R' are hydrogen, lower alkyl or aryl; X is lower alkoxy or the same as X'; Y is chlorine or the same as X; X' is aryloxy; Z is a 1,2- or 1,3-propylenedioxy (that may optionally carry hydroxy, lower alkyl or lower hydroxyalkyl substituents), or arylenedioxy radical; n is integer from three to nine; m is (n-1).Type: GrantFiled: February 10, 1978Date of Patent: May 6, 1980Assignee: General Electric CompanyInventors: Victor Mark, Lawrence C. Mitchell, Charles V. Hedges
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Patent number: 4182915Abstract: Process for the preparation of nucleophilically ring-substituted aromatic compounds from an aromatic-thallium (III) metallate is provided in which the aromatic-thallium (III) metallate is contacted with a source of the nucleophile to form the desired substituted aromatic compound, which may be recovered from the reaction mixture as by distillation. Exemplary processes include the preparation of aniline and phenol from benzene.Type: GrantFiled: January 24, 1977Date of Patent: January 8, 1980Assignee: Halcon International, Inc.Inventor: Robert J. Harvey
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Patent number: 4174460Abstract: A process for the hydroxylation of phenols and phenol ethers in the nucleus with hydrogen peroxide wherein a phenol or a phenol ether is reacted at the start of the reaction with substantially anhydrous hydrogen peroxide and wherein the reaction is carried out in the presence of a strong acid.Type: GrantFiled: March 31, 1977Date of Patent: November 13, 1979Assignee: Bayer AktiengesellschaftInventors: Hermann Seifert, Helmut Waldman, Wulf Schwerdtel, Wolfgang Swodenk
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Patent number: 4160113Abstract: The present invention is related to a process for the manufacture of resorcinols by catalytic dehydrogenation of cyclohexane diones-(1,3) in the liquid phase by means of a dehydrogenating mixture consisting of a solvent and of a catalyst containing a noble metal from Group VIII of the Periodic Table.Type: GrantFiled: November 11, 1977Date of Patent: July 3, 1979Assignee: Hoechst AktiengesellschaftInventors: Werner H. Muller, Knut Riedel, Hans Krekeler
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Patent number: 4147726Abstract: An organic hydroperoxide is hydrolyzed by acid-catalysis in a reaction medium comprising essentially a mixture of a polar solvent, e.g. a low boiling, low molecular weight alcohol and/or sulfolane and phenol. Specifically cyclohexanone and phenol are obtained from cyclohexylbenzene hydroperoxide.Type: GrantFiled: November 8, 1976Date of Patent: April 3, 1979Assignee: Phillips Petroleum CompanyInventor: Yulin Wu
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Patent number: 4147872Abstract: Azacycloalkanes, and derivatives thereof, including unsaturated analogs, each of which has at the 3-position a 2-hydroxy-4-substituted phenyl group wherein the 4-position substituent is alkyl which can have an oxygen atom as part of the chain, or aralkyl which can have an oxygen atom as part of the alkyl chain, their use for pharmacological and medicinal purposes, intermediates therefor and processes for their preparation.Type: GrantFiled: September 13, 1977Date of Patent: April 3, 1979Assignee: Pfizer Inc.Inventors: Thomas H. Althuis, Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
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Patent number: 4117243Abstract: A process for preparing o-benzylphenol is disclosed. The process comprises heating benzyl phenyl ether, either in liquid or vapor phase, in the presence of an effective amount of activated alumina catalyst.Type: GrantFiled: March 7, 1977Date of Patent: September 26, 1978Assignee: Continental Oil CompanyInventors: Charles M. Starks, Allan J. Lundeen
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Patent number: 4105698Abstract: A process for preparing ortho-substituted cinnamyl phenols is disclosed. The process comprises heating a mixture of cinnamyl alcohol and phenol in the presence of an effective amount of activated alumina.Type: GrantFiled: February 16, 1977Date of Patent: August 8, 1978Assignee: Continental Oil CompanyInventors: Charles M. Starks, Allan J. Lundeen
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Patent number: 4105699Abstract: A process for preparing o-benzylphenol in high selectivity is disclosed. The process comprises heating a mixture of benzyl alcohol and phenol in the presence of an effective amount of activated alumina as a catalyst.Type: GrantFiled: February 16, 1977Date of Patent: August 8, 1978Assignee: Continental Oil CompanyInventor: Charles M. Starks
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Patent number: 4098829Abstract: Polymeric hydroquinones of the structure ##STR1## WHEREIN N IS FROM 3 TO 10,000 INCLUSIVE AND R and R' independently are hydrogen or a lower alkyl, are disclosed, as is the preparation and the use of such materials, especially as nonabsorbable polymeric antioxidants for edible materials.Type: GrantFiled: May 19, 1977Date of Patent: July 4, 1978Assignee: DynapolInventors: Ned M. Weinshenker, James A. Dale
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Patent number: 4091225Abstract: This invention comprises an alkylation, reduction and transesterification process for the preparation of ester substituted phenols. The products are useful as antioxidants and may be prepared in high yields and with a high degree of purity.Type: GrantFiled: January 22, 1974Date of Patent: May 23, 1978Assignee: The Goodyear Tire & Rubber CompanyInventor: Dane K. Parker
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Patent number: 4087554Abstract: The disclosure relates to a method for use in the practice of animal husbandry which comprises the oral administration to non-ruminant animals of an iodonium salt. Solid or liquid compositions of said iodonium salts for use in the said method are also disclosed. Certain of the iodonium sats used in the said method are novel compounds.Type: GrantFiled: October 14, 1975Date of Patent: May 2, 1978Assignee: Imperial Chemical Industries LimitedInventors: David Bryan Haydock, Michael James Smithers
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Patent number: 4087410Abstract: 2,6-Dimethoxyphenol reacts with a tertiary carbinol in the presence of an acid to provide exclusively a 1-hydroxy-2,6-dimethoxy-4-tertiary alkyl)benzene, which when reacted with a halogenated disubstituted phosphite affords a 2,6-dimethoxy-4-tertiary alkyl)phenyl disubstituted phosphate. Reduction of the phenyl phosphate derivative by reaction with an alkali metal affords a 1-(tertiary alkyl)-3,5-dimethoxybenzene, which upon reaction with a demethylating agent provides a 5-(tertiary alkyl)resorcinol.Type: GrantFiled: June 14, 1976Date of Patent: May 2, 1978Assignee: Eli Lilly and CompanyInventors: Samuel J. Dominianni, Charles W. Ryan