Oxy Containing Reactant Patents (Class 568/322)
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Patent number: 5023381Abstract: A process is described for the preparation of 2-methoxy-6-propionyl-naphthalene, an intermediate in the synthesis of naproxen.The process consists of Friedel-Crafts acylation of 2-methoxy-naphthalene, and obviates the drawbacks related to the use of nitrobenzene as solvent.Type: GrantFiled: December 20, 1989Date of Patent: June 11, 1991Assignee: Zambon Group S.p.A.Inventors: Giulio Perdoncin, Claudio Giordano, Maurizio Paiocchi, Roberto Casagrande
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Patent number: 5019655Abstract: Method of preparing 4-disubstituted phenyl-1-tetralones of formula ##STR1## in which X represents halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy and Y, situated in position 2' or 3', represents halogen or C.sub.1 -C.sub.4 alkyl, this method being characterized in that it comprises the reaction, in the presence of an acid agent, of .alpha.-naphthol of formula (II) with a phenyl compound of formula (III): ##STR2## where X represents halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, and Y is situated in the ortho or meta position with respect to X and represents halogen or C.sub.1 -C.sub.4 alkyl.Type: GrantFiled: June 8, 1989Date of Patent: May 28, 1991Assignee: Delalande S.A.Inventor: Guy P. Adrian
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Patent number: 5008461Abstract: Benzyl ketones of the general formula I ##STR1## where R.sup.1 is C.sub.1 -C.sub.8 -alkyl which is unsubstituted or substituted by cycloalkyl or aryl and R.sup.2 and R.sup.3 are each halogen, C.sub.1 -C.sub.4 -alkyl, hydroxyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.2 -C.sub.4 -methylenedioxy, are prepared by a process in which a glycol monoether of the general formula II ##STR2## where R.sup.1, R.sup.2 and R.sup.3 have the abovementioned meanings and R.sup.4 is C.sub.1 -C.sub.8 -alkyl, is converted in the presence of silica, a phosphate or a zeolite at from 50.degree. to 500.degree. C. and under from 0.01 to 50 bar.Type: GrantFiled: March 7, 1990Date of Patent: April 16, 1991Assignee: BASF AktiengesellschaftInventors: Fritz Naeumann, Eckhard Hickmann
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Patent number: 4990680Abstract: A process for the preparation of 2,4-dihydroxybenzophenone by reacting resorcinol with benzotrichloride in water, wherein the reaction mixture contains a surfactant or a dispersing or emulsifying agent in a concentration of from 0.05 to 5%, by weight of the water.The product is obtained in high yield and good purity.Type: GrantFiled: January 11, 1990Date of Patent: February 5, 1991Assignee: BASF AktiengesellschaftInventors: Peter Neumann, Alexander Aumueller
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Patent number: 4982006Abstract: The present invention involves process for the preparation of compounds having the chemical structure: ##STR1## wherein Ar--H is an aromatic compound which is activated to an electrophilic attack, and wherein --Y is an aliphatic group having a labile moiety, especially where the labile moiety is a terminally unsaturated moiety: --C.tbd.CH, ##STR2## or aldehydes in the form of their acetals. The process comprises the step of reacting Ar--H and ##STR3## wherein --X is --Cl or --Br, and where the reaction step is carried out in a solvent medium at a temperature of from about -40.degree. C. to about -100.degree. C. using stannic chloride as a catalyst.Type: GrantFiled: May 1, 1989Date of Patent: January 1, 1991Assignee: Norwich Eaton Pharmaceuticals, Inc.Inventor: Thomas T. Hudec
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Patent number: 4967011Abstract: The present invention relates to a process for decomposing an aromatic acylated compound.HF-BF.sub.3 complex in preparing an aromatic acylated compound by decomposing an aromatic acylated compound.HF-BF.sub.3 complex obtained by reacting an aromatic compound with an acylating agent in the presence of HF-BF.sub.3 as a catalyst, which comprises subjecting the aromatic acylated compound.HF-BF.sub.3 complex to thermal decomposition in the presence of at least one aromatic hydrocarbon (A.H.) selected from benzene, toluene and chlorobenzene and at least one saturated aliphatic hydrocarbon (S.H.) selected from pentane, hexane and cyclohexane, as a decomposing agent.Type: GrantFiled: August 11, 1989Date of Patent: October 30, 1990Assignee: Mitsubishi Gas Chemical Co., Inc.Inventors: Nobuyuki Tokura, Tadayoshi Takefumi, Shunichi Matsumoto, Tatsuhiko Yanagawa, Yoshihiro Shiokawa, Ichiyo Ohtsuka
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Patent number: 4967009Abstract: This invention relates to a method for manufacturing aromatic compounds having the following formula (II) comprising the step of reacting an unsaturated aromatic compound having the following formula (I) with an aryl compound containing an iodosyl group or the salt thereof within a temperature range of from -50.degree. to 200.degree. C.Type: GrantFiled: July 7, 1989Date of Patent: October 30, 1990Assignee: Nippon Petrochemicals Co., Ltd.Inventors: Isoo Shimizu, Yasuo Matsumura, Kouichi Iwamoto
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Patent number: 4960943Abstract: Phenylketones etherified in the 4-position can be prepared by reaction of aromatic ethers which have a free 4-position with acylating agents, the acylation being carried out in the presence of zeolite catalysts having pore sizes of at least 5 .ANG..Type: GrantFiled: March 2, 1989Date of Patent: October 2, 1990Assignee: Bayer AktiengesellschaftInventors: Artur Botta, Hans-Josef Buysch, Lothar Puppe, Dieter Arlt
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Patent number: 4922026Abstract: Aromatic diketones are prepared by a process comprising contacting at least one acylatable aromatic compound and at least one aromatic diacyl halide in the presence of catalytic amounts of ferric chloride or ferric oxide at an elevated temperature and at superatmospheric conditions.Type: GrantFiled: December 27, 1988Date of Patent: May 1, 1990Assignee: The Dow Chemical CompanyInventors: Robert B. Baker, Jr., R. Garth Pews, Eric W. Otterbacher, James A. Gall
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Patent number: 4918237Abstract: 1,4-Bis(4-phenoxybenzoyl)benzene is made in a homogeneous or heterogeneous system by a reaction of diphenyl ether with 1,4-benzenedicarbonyl chloride at 220.degree.-258.degree. C. in the presence of certain iron, gallium, and indium compounds in catalytic amounts. The mole ratio of diphenyl ether to 1,4-dicarbonyl chloride is 5:1 to 25:1 and the mole ratio of 1,4-benzenedicarbonyl chloride to the catalyst is 1000:1 to 10:1.Type: GrantFiled: March 13, 1989Date of Patent: April 17, 1990Assignee: E. I. du Pont de Nemours and CompanyInventors: David R. Corbin, Enio Kumpinsky
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Patent number: 4906658Abstract: Compounds of Formula I ##STR1## the pharmaceutically acceptable salts, and the gamma-lactone form thereof are described. They are antagonists of leukotrienes and SRS-A.Type: GrantFiled: April 21, 1987Date of Patent: March 6, 1990Assignee: Merck Frosst Canada, Inc.Inventors: Haydn W. R. Williams, Robert N. Young
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Patent number: 4898983Abstract: Friedel Crafts preparation of aryl carbonyl compounds having an exceptionally high degree of isomeric purity and freedom from by-products can be achieved by adding to the Lewis acid reaction system a protic controlling agent selected from ROX, water, RCOOX, RSO.sub.3 X, and ROY, wherein R is organic, X is hydrogen or metal, and Y is metal. Contrary to conventional expectation, the protic agent does not significantly alkylate or acylate the Friedel Crafts reaction product.Type: GrantFiled: November 7, 1988Date of Patent: February 6, 1990Assignee: Raychem LimitedInventor: Ian D. H. Towle
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Patent number: 4898988Abstract: A process for the preparation of .beta.-hydroxyketones comprising the catalytic hydrogenolysis of an aqueous solution of isoxazolines having the formula ##STR1## in a fixed bed reactor containing a transition metal catalyst at a temperature between 20.degree. to 150.degree. C. and a pressure from about 0 to 150 psig; wherein R.sub.1 and R.sub.2 are independently selected from hydrogen, alkyl, cycloalkyl or aromatic group and wherein the aqueous solution of isoxazolines is substantially free of acids or buffers.Type: GrantFiled: March 13, 1989Date of Patent: February 6, 1990Assignee: W. R. Grace & Co.-Conn.Inventors: You-Jyh Lin, Harold Kloczewski
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Patent number: 4868338Abstract: The acylation of a naphthalene compound, substituted in the 2-position with an electron-donating group, with a reactive derivative of a lower aliphatic acid, in an aprotic organic diluent and in the presence of a Friedel Crafts catalyst consisting of a halide of an element having at least two valences, is improved when maintaining constant at any time the molar ratio of the naphthalene compound to the acylating agent and that of the acylating agent to the Friedel Crafts catalyst within specific ranges.Type: GrantFiled: March 8, 1988Date of Patent: September 19, 1989Assignee: Blaschim S.p.A.Inventors: Ambrogio Magni, Giuseppina Visentin
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Patent number: 4868337Abstract: A process for synthesizing an optically pure ketone comprising the steps of: treating an appropriate optically pure boronic ester with an organolithium compound at -78.degree. C. to obtain the "ate" complex, separating the optically pure borinic ester from the complex and converting said borinic ester into an optically pure ketone represented by the formulae:R*COR.sup.1 and R*COC.tbd.CR.sup.1wherein R* is a chiral organyl moiety and R.sup.1 is an achiral organyl moeity.Type: GrantFiled: December 17, 1987Date of Patent: September 19, 1989Assignee: Aldrich-Boranes, Inc.Inventor: Herbert C. Brown
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Patent number: 4845302Abstract: 5H-Dibenzo[a,d]cyclohepten-5-ones (I) ##STR1## (A and B being radicals for completing aromatic ring systems) are prepared by converting (Z)-2-(2-arylethenyl)arylcarboxylic acids (II) ##STR2## or E/Z-isomer mixtures thereof with a halogenating agent for carboxylic acids at from (-30.degree.) to +120.degree. C. to the corresponding carbonyl halides (III) ##STR3## where X is halogen, and cyclizing said carbonyl halides at from 0.degree. to 100.degree. C. in the presence of a Lewis acid.Type: GrantFiled: December 18, 1987Date of Patent: July 4, 1989Assignee: BASF AktiengsellschaftInventors: Marco Thyes, Gerd Steiner
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Patent number: 4843179Abstract: A method of preparing 4,4'-diphenoxybenzophenone, comprising reacting diphenyl ether and carbon dioxide in the presence of a Friedel-Crafts catalyst and a promoting agent, preferably selected from the group consisting of phosphoryl chloride, phosphorus pentoxide, tetrachlorosilane, methyltrichlorosilane, dimethyldichlorosilane, titanium tetrachloride, zirconium tetrachloride, zirconium oxyhalide, and phosphorus pentachloride. In a preferred embodiment, the Friedel-Crafts catalyst is aluminum chloride and the promoting agent is phosphoryl chloride.Type: GrantFiled: January 5, 1988Date of Patent: June 27, 1989Assignee: Raychem CorporationInventors: Viktors Jansons, Heinrich C. Gors
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Patent number: 4835319Abstract: 1,4-Bis(4-phenoxybenzoyl)benzene is made in a heterogeneous system by a reaction of diphenyl ether with 1,4-benzenedicarbonyl chloride at 190.degree.-250.degree. C. in the presence of a zeolite catalyst having a ring structure containing 12 oxygen atoms, which can be either an activated zeolite in hydrogen form or an iron-exchanged zeolite, which zeolite can be readily separated from the hot liquid phase in the reaction mixture. The mole ratio of diphenyl ether to 1,4-dicarbonyl chloride, when the catalyst is in hydrogen form, is about 50-80:1; when the catalyst is in iron-exhcanged form, it is about 10-50:1, and the weight ratio of 1,4-benzenedicarbonyl chloride to zeolite in hydrogen form is 3:1 to 1:2, while the ratio of 1,4-benzenedicarbonyl chloride to zeolite in iron-exchanged form is 10:1 to 1:32. The product readily crystallizes in a high state of purity from the cooled solution. 1,4-Bis(4-phenoxybenzoyl)benzene is a vaulable intermediate in the synthesis of polyetherketone resins.Type: GrantFiled: July 14, 1988Date of Patent: May 30, 1989Assignee: E. I. Du Pont de Nemours and CompanyInventors: David R. Corbin, Enio Kumpinsky, Antonio Vidal
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Patent number: 4835318Abstract: A process for the preparation of arylperfluoroalkyl ketones of the general formula I ##STR1## wherein R.sup.1 and R.sup.5 represent at least one of the substituents hydrogen, halogen, alkyl, alkoxy, alkylthio and perfluorinated alkyl, each having from 1 to 6 carbon atoms and n is an integer from 1 to 6, which comprises reacting an aryl carbonyl compound having the general formula II ##STR2## wherein R.sup.1 to R.sup.5 have the above-mentioned meaning and X as a monovalent moiety represents fluorine, chlorine or bromine and as a bivalent moiety the oxygen atom of an anhydride bridge, with a perfluoroalkyl halide of the general formula C.sub.n F.sub.2n+1 -Hal (III), wherein Hal represents chlorine, bromine or iodine and n is an integer from 1 to 6, in the presence of a trisdialkyl amide of phosphorus acid of the general formula P[N(alkyl)2]3 (IV).Type: GrantFiled: July 28, 1988Date of Patent: May 30, 1989Assignee: Hoechst AktiengesellschaftInventors: Alfred Kruse, Gunter Siegemund, Klaus Schlich, Ingo Ruppert, deceased
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Patent number: 4827041Abstract: A process for manufacturing 1,4-bis(4-phenoxybenzoyl)benzene, wehrein diphenyl ether is contacted for about 30-360 minutes at 130.degree.-200.degree. C. with 1,4-benzenedicarbonyl chloride in respective mole ratios of about 15-80:1 in the presence of a fluorocarbon resin carrying pendant sulfonic acid groups, the weight ratio of the resin to 1,4-benzenedicarbonyl chloride being 3:1-1:2; the hot solution is separated from the resin, and the crystalline product is recovered from the solution on cooling. The so obtained 1,4-bis(4-phenoxybenzoyl)-benzene is a high purity material free of ortho-isomer and catalyst contamination and can be used without further purification as one of the starting materials in the preparation of polyetherketones, which are important engineering resins.Type: GrantFiled: March 10, 1988Date of Patent: May 2, 1989Assignee: E. I. Du Pont de Nemours and CompanyInventors: Thomas M. Ford, Enio Kumpinsky, Antonio Vidal
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Patent number: 4824612Abstract: Aromatic ketones or .alpha.-diketones can be prepared from the corresponding carbinols by reaction with molar amounts of a sulfonyl chloride in the presence of a base. The corresponding sulfinic acid or salt thereof with the base is formed simultaneously.Type: GrantFiled: December 7, 1987Date of Patent: April 25, 1989Assignee: Ciba-Geigy CorporationInventors: Werner Rutsch, Mario Slongo
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Patent number: 4814508Abstract: Aromatic carbonyl compounds, in particular arylene ether ketones, are prepared by reacting an appropriate reagent system in the presence of free Lewis acid and a complex between a Lewis acid, for example, aluminum trichloride, and a Lewis base, for example, N,N-dimethylformamide, and, optionally, a diluent, such as methylene chloride. The process is particularly advantageous for the preparation of substantially or all para-linked arylene ether ketones as the presence of the Lewis acid/Lewis base complex markedly reduces alkylation and ensures the substantial absence of ortho substitution.Type: GrantFiled: March 21, 1988Date of Patent: March 21, 1989Assignee: Raychem CorporationInventors: Heinrich C. Gors, Patrick J. Horner, Viktors Jansons
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Patent number: 4803013Abstract: Novel halogenated naphthalene derivatives of the formula ##STR1## where X is F or Br, and a process for making the same are disclosed. Insulating oils are also disclosed which essentially comprise such a fluorine-containing compound and commonly used hydrocarbon insulating oils. The additive is highly conductive to improved dielectric constant, dielectric loss, hydrogen gas absorptivity, fluidity and viscosity characteristics.Type: GrantFiled: March 16, 1988Date of Patent: February 7, 1989Assignee: Nippon Oil Co., Ltd.Inventor: Nobuo Yokoyama
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Patent number: 4772714Abstract: Disclosed is a process for the preparation of alpha-aryl and alpha-heteroaryl ketones useful as intermediates in the synthesis of various pharmaceutical and agricultural chemicals, which process operates according to the following reaction scheme: ##STR1##Type: GrantFiled: July 7, 1986Date of Patent: September 20, 1988Assignee: Agency of Industrial Science & TechnologyInventors: Masato Tanaka, Toshiyasu Sakakura
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Patent number: 4764642Abstract: A process is described for preparing alpha-haloalkyl-aryl-ketones, comprising reacting a substantially anhydrous strong acid with a ketal of formula ##STR1## in which Ar, R, R.sub.1, R.sub.2 and X have the meanings given in the description.Type: GrantFiled: October 6, 1986Date of Patent: August 16, 1988Assignee: Zambon S.p.A.Inventors: Graziano Castaldi, Silvia Cavicchioli, Claudio Giordano
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Patent number: 4694111Abstract: The production of a 1-hydroxy-2-lower alkoxyalkyl benzene, e.g. 2-(1'-methoxyethyl) phenol, is carried out by reacting phenol with a lower acetal or ketal, e.g., 1,1-dimethoxyethane at an elevated temperature in the presence of an H-ZSM-5 zeolite, as catalyst.Type: GrantFiled: July 9, 1986Date of Patent: September 15, 1987Assignee: Celanese CorporationInventor: Balaram B. G. Gupta
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Patent number: 4670603Abstract: Preparation of aryl alkyl ketones by reaction of an aryl compound with an aliphatic acid and/or a functional derivative thereof in anhydrous hydrofluoric acid.Type: GrantFiled: September 24, 1985Date of Patent: June 2, 1987Assignee: Blaschim S.p.A.Inventors: Oreste Piccolo, Giuseppina Visentin, Pietro Blasina, Franca Spreafico
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Patent number: 4665246Abstract: The process of producing ethynyl aromatic compounds which are useful as intermediates in the preparation of 3-dimensional carbon-carbon structures for aerospace and military applications and as starting materials in the preparation of organic semi-conductors. The ethynyl aromatic compounds may be any of the classes illustrated in FIGS. 1, 2 and 3 of the drawing. Starting compounds for the process may by any compound from the classes illustrated in FIGS. 4, 5 and 6. The starting compound is reacted in the presence of a Friedel-Crafts catalyst in a suitable solvent with an acyl compound from the class illustrated in FIG. 7 to yield a compound within the classes illustrated in FIGS. 8, 9 and 10. The carbonyl groups in this compound are reduced to yield a corresponding alcohol. Each hydroxy group in the alcohol is converted to an easily eliminatable group, e.g., by reacting it with methane sulfonyl chloride, when subjected to basic conditions.Type: GrantFiled: March 9, 1984Date of Patent: May 12, 1987Assignee: Chem Biochem Research, Inc.Inventor: Chris Anderson
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Patent number: 4647702Abstract: A method for the dehydroxylation of alpha-hydroxyketone using lithium diphenylphosphide. The alpha-hydroxyketone, e.g. benzoin, is reacted with a solution of lithium diphenylphosphide followed by the addition of either an alkyl halide, e.g. methyliodide, or an alkyl halide and an organic acid, e.g. acetic acid, to yield the dehydroxylated compound, e.g. desoxybenzoin.Type: GrantFiled: November 18, 1985Date of Patent: March 3, 1987Assignee: Stauffer Chemical CompanyInventor: Andrea Leone-Bay
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Patent number: 4628120Abstract: A preparing method of optically active ketones given by a general formula ##STR1## (wherein R represents a hydrocarbon group having 2 to 20 carbon atoms and R' represents a hydrocarbon group having 1 to 20 carbon atoms. The hydrocarbon groups of R and R' may contain functional groups having no influence on the reaction. But, * represents an asymmetric carbon atom, and R represents a more electron donating group than R' (except when R=R') through the rearrangement reaction by using organoaluminum compound.Type: GrantFiled: October 16, 1984Date of Patent: December 9, 1986Assignee: Toyo Stauffer Chemical Co., Ltd.Inventors: Genichi Tsuchihashi, Keisuke Suzuki
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Patent number: 4618724Abstract: This invention deals with the use of a perfluorocarbon polymer oxidation catalyst consisting of a perfluorocarbon main chain and a side chain constructed from structural units of chromium (III) difluoromethylene sulfonate or cerium (IV) difluoromethylene sulfonate in a method of preparing a carbonyl compound through an oxidation of an alcohol.Type: GrantFiled: February 11, 1985Date of Patent: October 21, 1986Assignee: E. I. Du Pont de Nemours and CompanyInventors: Hitosi Nozaki, Koichiro Oshima
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Patent number: 4618726Abstract: A process for the preparation of benzophenones. A compound of the formula COX.sub.4 X.sub.5, where X.sub.4 and X.sub.5, which may be identical or different are halogen atoms, is reacted, in liquid hydrofluoric acid, with a deactivated benzene derivative, in the presence of boron trifluoride in such amount that the absolute pressure of boron trifluoride in the reaction space is at least one bar.Type: GrantFiled: December 18, 1984Date of Patent: October 21, 1986Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Michel Desbois
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Patent number: 4616095Abstract: Described is an isomer-directed process for producing asymmetric ketones defined according to the generic structure: ##STR1## wherein one of Z.sub.1 or Z.sub.2 is the moiety: ##STR2## and the other of Z.sub.1 or Z.sub.2 is hydrogen; wherein R.sub.11 and R.sub.21 represent hydrogen or the same or different alkyl or alkenyl with the proviso that R.sub.11 and R.sub.21 are not both hydrogen or wherein R.sub.11 and R.sub.21 taken together:(i) complete a cycloalkyl, cycloalkenyl, bicycloalkyl, mono or polyalkyl cycloakyl or mono or polyalkyl cycloalkenyl ring, or(ii) represent alkylidene, cycloalkenyl alkylidene, aralkylidene, mono or polyalkyl cycloalkenyl alkylidene or mono or polyalkyl aralkylidene;and wherein R.sub.6, R.sub.7 and R.sub.Type: GrantFiled: August 13, 1985Date of Patent: October 7, 1986Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Robert P. Belko, William L. Schreiber, Michael Licciardello
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Patent number: 4613706Abstract: Described is an isomer-directed process for producing asymmetric ketones defined according to the generic structure: ##STR1## wherein one of Z.sub.1 or Z.sub.2 is the moiety: ##STR2## and the other of Z.sub.1 or Z.sub.2 is hydrogen; wherein R.sub.11 and R.sub.21 represent hydrogen or the same or different alkyl or alkenyl with the proviso that R.sub.11 and R.sub.21 are not both hydrogen or wherein R.sub.11 and R.sub.21 taken together:(i) complete a cycloalkyl, cycloalkenyl, bicycloalkyl, mono or polyalkyl cycloalkyl or mono or polyalkyl cycloalkenyl ring, or(ii) represent alkylidene, cycloalkenyl alkylidene, aralkylidene, mono or polyalkyl cycloalkenyl alkylidene or mono or polyalkyl aralkylidene;and wherein R.sub.6, R.sub.7 and R.sub.Type: GrantFiled: August 13, 1985Date of Patent: September 23, 1986Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Robert P. Belko, William L. Schreiber, Michael Licciardello
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Patent number: 4604486Abstract: A method of preparing optically active ketones having the general formula ##STR1## wherein R.sup.2 and R.sup.3 indicate hydrocarbon groups having 1 to 20 carbon atoms characterized by submitting an optically active sulfonyloxy alcohol having the general formula ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 indicate hydrocarbon groups having carbon atoms of 1 to 20 and which optionally contain N, O, P and S. The symbol * indicates asymmetric carbon atoms to rearrangement in a solvent and in the presence of organoaluminum compounds given by the general formula R.sub.3-n.sup.4 AlX.sub.n, (wherein R.sup.4 indicates an alkyl group having carbon atoms of 1 to 20 and X indicates a halogen atom, an alkoxy group or a CN group. n is 1, 1.5 or 2).Type: GrantFiled: January 4, 1985Date of Patent: August 5, 1986Assignee: Toyo Stauffer Chemical Co., Ltd.Inventors: Genichi Tsuchihashi, Keisuke Suzuki
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Patent number: 4604485Abstract: Preparation of para-substituted 4-hydroxybenzophenones by forming poly(4-oxybenzoyl) in situ and reacting it with an appropriately substituted aromatic compound. The poly(4-oxybenzoyl) can be formed from a precursor such as 4-hydroxybenzoic acid by reaction with an agent which removes water from the acid to form the polymer. The reaction with the appropriately substituted aromatic compound, for example fluorobenzone, is effected in the presence of a Lewis acid compound such as aluminum chloride.Type: GrantFiled: June 4, 1984Date of Patent: August 5, 1986Assignee: Imperial Chemical Industries PLCInventor: Howard M. Colquhoun
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Patent number: 4599452Abstract: Preparation of para-substituted 4-hydroxybenzophenones by reacting appropriately substituted aromatic compound with poly(4-oxybenzoyl) in the presence of an acid catalyst. The reaction with the appropriately substituted aromatic compound, for example fluorobenzene, is effected in the presence of an acid catalyst such as a strong proton acid or a Lewis Acid or a mixture thereof.Type: GrantFiled: June 4, 1984Date of Patent: July 8, 1986Assignee: Imperial Chemical Industries PLCInventors: Howard M. Colquhoun, Alan G. Breeze
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Patent number: 4593125Abstract: Naphthalene substituted in the 2- or .beta.-position with an electron-donating substituent can be acylated with high regioselectivity in the 6-position by using an acylating agent in substantially anhydrous hydrogen fluoride which functions both as catalyst and solvent.Type: GrantFiled: March 13, 1985Date of Patent: June 3, 1986Assignee: Celanese CorporationInventors: Kenneth G. Davenport, H. Clay Linstid, III
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Patent number: 4568768Abstract: A method for producing m-hydroxy-acetophenone which comprises allowing m-(2-hydroxy-2-propyl)cumene hydroperoxide to react at 30.degree. to 100.degree. C. in the presence of an aqueous solution containing 0.001 to 1 mole of iron salt per mole of said compound, 0.01 to 4 moles of copper salt per mole of said iron salt, and mineral acid to give m-(2-hydroxy-2-propyl)acetophenone, then allowing the resulting compound to react at 30.degree. to 95.degree. C. in the presence of 1 to 20 moles of 5 to 90% by weight aqueous hydrogen peroxide solution per mole of said compound and acid catalyst to form m-(2-hydroperoxy-2-propyl)acetophenone, and further subjecting the product formed to acid decomposition. m-Hydroxyacetophenone is an important intermediate in the fields of pharmaceuticals, agricultural chemicals, dyestuffs and the like.Type: GrantFiled: December 13, 1984Date of Patent: February 4, 1986Assignee: Sumitomo Chemical Company, LimitedInventors: Makoto Nakamura, Seiichi Kai, Nobuharu Kono
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Patent number: 4568429Abstract: 2,4-Dihydroxybenzophenone is prepared substantially quantitatively and in a highly purified form by reacting resorcinol with a benzotrihalide in the presence of an aqueous solution of N-methylpyrrolidone and subsequently subjecting the crude reaction product mixture to vacuum distillation.Type: GrantFiled: March 2, 1984Date of Patent: February 4, 1986Assignee: GAF CorporationInventor: Kou-Chang Liu
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Patent number: 4562287Abstract: Therapeutic compositions having anti-inflammatory and analgesic activity, containing as active compound 2-(4-biphenylyl)-4-hexenoic acid and/or derivatives thereof, characterized by low toxicity and by the absence or minimum level of ulcerogenic effect.Type: GrantFiled: May 29, 1984Date of Patent: December 31, 1985Assignee: Scharper S.p.A. per l'Industria FarmaceuticaInventors: Alfonso Del Vecchio, Grazia Sestini
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Patent number: 4562294Abstract: Spiro[5.5]undeca-1,4,8-trien-3-ones are prepared by heating a reaction mixture consisting essentially of a 4-aminomethylphenol, a conjugated diene, and an inert solvent at a temperature of at least about 190.degree. C.Type: GrantFiled: October 15, 1984Date of Patent: December 31, 1985Assignee: Ethyl CorporationInventor: Jerry M. Roper
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Patent number: 4560805Abstract: An improved process is provided for forming ketones from the corresponding olefins in the vapor phase in the presence of water vapor employing a heterogeneous catalyst comprising rhenium compounds and complexes, optionally containing at least one metal compound or complex selected from the group consisting of Group VIB metals and Group VIII noble metals, and mixtures thereof. It has been surprisingly found that these catalysts effect the formation of ketones in high selectivities with minimal selectivities to the undesirable carbon dioxide and carbon monoxide by-products.Type: GrantFiled: July 25, 1983Date of Patent: December 24, 1985Assignee: Exxon Research & Engineering Co.Inventors: Chuen Y. Yeh, Charles Savini
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Patent number: 4551554Abstract: A new process for production of 2-haloacetylphenols having the general formula ##STR1## (wherein, Y is halogen atom;m is an integer of 0-2,X and n have the same meaning as mentioned below),which comprises reacting phenols having the general formula ##STR2## (wherein, X is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.5 alkoxy or halogen atom;n is an integer of 0-2)with haloacetonitriles and boron halide compounds in the presence of condensing coagents.Type: GrantFiled: September 23, 1981Date of Patent: November 5, 1985Assignee: Shionogi & Co., Ltd.Inventors: Tsutomu Sugasawa, Tatsuo Toyoda, Kazuyuki Sasakura
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Patent number: 4524221Abstract: Process for the production of an acyloin comprising the steps of:A. reacting a Grignard reagent with silylated cyanohydrin,B. treating the reaction product of step A with aqueous acid, andC. recovering the resulting acyloin.Acyloins thus formed are useful as photoinitiators for initiation of free radical polymerization reactions.Type: GrantFiled: February 22, 1983Date of Patent: June 18, 1985Assignee: Minnesota Mining and Manufacturing CompanyInventors: Steven M. Heilmann, Larry R. Krepski, Jerald K. Rasmussen
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Patent number: 4510329Abstract: A process for preparing cyclopentenolones of the formula ##STR1## wherein R.sub.1 is an alkyl group having not more than 6 carbon atoms, an alkenyl or alkynyl group having not more than 6 carbon atoms or a group of the formula: ##STR2## in which R.sub.2 is a hydrogen atom, a methyl group or a halogen atom directly from the corresponding furan-carbinols of the formula: ##STR3## wherein R.sub.1 is as defined above in a single step with an excellent yield, characterized in that the furan-carbinols are treated with water in the presence or absence of a catalyst.Type: GrantFiled: November 28, 1980Date of Patent: April 9, 1985Assignee: Sumitomo Chemical Company, LimitedInventors: Kenji Saito, Hiroshi Yamachika
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Patent number: 4508924Abstract: o-Acylphenols and p-acylphenols are prepared by reacting phenol with an acid halide and aluminum chloride, using a halobenzene as the solvent, at from 15.degree. to 55.degree. C. and then at from 55.degree. and 200.degree. C.The compounds obtainable by the process of the invention are valuable starting materials for the preparation of drugs, pesticides and dyes.Type: GrantFiled: November 1, 1983Date of Patent: April 2, 1985Assignee: BASF AktiengesellschaftInventors: Josef Mueller, Walter-Wielant Wiersdorff, Werner Kirschenlohr, Gerd Schwantje
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Patent number: 4496767Abstract: A novel process for preparing 2-cyclopentenones of the formula: ##STR1## wherein R.sub.1 is hydrogen, alkyl or alkenyl and R.sub.2 is alkyl, alkenyl, alkynyl, cycloalkyl, aryl or aralkyl, which comprises esterifying a mixture of a 3-hydroxy-4-cyclopentenone of the formula: ##STR2## wherein R.sub.1 and R.sub.2 are each as defined above and a 4-hydroxy-2-cyclopentenone of the formulas: ##STR3## wherein R.sub.1 and R.sub.2 are each as defined above with an aliphatic carboxylic acid to give a mixture of the 4-hydroxy-2-cyclopentenone (III) and the cyclopentenone ester of the formula: ##STR4## wherein R.sub.1 and R.sub.2 are each as defined above and R is hydrogen or C.sub.1 -C.sub.4 alkyl and subjecting the resulting mixture to reduction.Type: GrantFiled: October 18, 1983Date of Patent: January 29, 1985Assignee: Sumitomo Chemical Company, LimitedInventors: Masayoshi Minai, Tadashi Katsura
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Patent number: 4495370Abstract: A process for the preparation of a 5-aryloxy-1-chloro-3,3-dimethyl-2-pentanone of the formula ##STR1## in which R.sup.1 and R.sup.2 each independently is halogen, alkyl having 1 to 4 carbon atoms, alkoxy or alkylthio each having 1 to 2 carbon atoms, halogenoalkyl, halogenoalkoxy or halogenoalkylthio each having 1 to 2 carbon atoms and 1 to 5 halogen atoms, cyclohexyl, dialkylamino having 1 to 4 carbon atoms in each alkyl moiety, nitro, cyano, alkoxy-carbonyl having 1 to 4 carbon atoms in the alkyl moiety, phenyl or halophenyl, m and n each independently is an integer from 0 to 5, and m+n.ltoreq.5,comprising reacting 1,1,5-trichloro-3,3-dimethyl-1-pentene of the formula ##STR2## with a phenol of the formula ##STR3## in the presence of a base in a diluent, to produce a compound of the formula ##STR4## and subjecting such reaction product to acid hydrolysis.Type: GrantFiled: May 27, 1983Date of Patent: January 22, 1985Assignee: Bayer AktiengesellschaftInventors: Manfred Jautelat, Dieter Arlt, Gerhard Jager
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Patent number: 4480133Abstract: Novel 2,4-dihydrocarbylspiro[5.5]undeca-1,4,8-trien-3-one compounds are prepared by reacting an N,N-dihydrocarbyl,2,6-dihydrocarbyl-4-aminomethylphenol with a conjugated diene and an alkyl halide in a liquid solvent medium.Type: GrantFiled: March 4, 1983Date of Patent: October 30, 1984Assignee: Ethyl CorporationInventor: Jerry M. Roper