Aldehyde Reactant Patents (Class 568/433)
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Patent number: 4716249Abstract: Described is a process for preparing natural benzaldehyde and acetaldehyde and compositions of matter containing natural benzaldehyde and acetaldehyde as well as products produced thereby and organoleptic utilities thereof, which process comprises the step of contacting with base naturally occurring cinnamaldehyde or a natural product rich in cinnamaldehyde such as Ceylon oil of cinnamon, Ceylon cinnamon bark, Saigon cinnamon bark, cassia oil, Ceylon cinnamon quills, cinnamon leaf oil, oil of cinnamon Madagascar or the like according to the reaction: ##STR1## the reaction taking place in the absence of any other reagents except inert solvent and ionic surfactant or emulsifier.Type: GrantFiled: October 31, 1986Date of Patent: December 29, 1987Assignee: International Flavors & Fragrances Inc.Inventor: Alan O. Pittet
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Patent number: 4705650Abstract: Compounds halogenated in the .alpha.-position to an electron-attracting group of formula ##STR1## in which X denotes a halogen atom, R denotes a hydrogen atom or a hydrocarbon radical or a radical --(CH.sub.2).sub.3 --COOR.sub.1 and Z denotes a radical --CHO, --COR.sub.2, --COOR.sub.3, --CONR.sub.4 R.sub.5, --CN, --SO.sub.2 R.sub.6, --NO.sub.2, --CO--(CH.sub.2)p--COO.sub.1 or --COO(CH.sub.2)p--COOR.sub.1 are made by a halogenating deacylation of a compound of formula ##STR2## in which R' denotes a hydrogen atom or a hydrocarbon radical, R" denotes a methyl radical and Z' denotes a radical --CHO, --COR.sub.2, --COOR.sub.3, --CONR.sub.4 R.sub.5, --CN, --SO.sub.2 R.sub.6 or --NO.sub.2 or R' and R" may form a radical --(CH.sub.2)-- or R' and R" may form a radical --CO--(CH.sub.2)p-- or --COO(CH.sub.2)p--, using an alkali metal alcoholate or an alkali or alkaline-earth metal carbonate and a halogenating agent.Type: GrantFiled: July 10, 1985Date of Patent: November 10, 1987Assignee: Rhone-Poulenc SanteInventors: Gerard Mignani, Didier Morel
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Patent number: 4700010Abstract: A catalytic process for the formylation, in the 2-position, of optionally substituted phenols, particularly 4-nonylphenol, using a catalyst comprising a tin phenoxide and a tertiary amine.Type: GrantFiled: August 7, 1985Date of Patent: October 13, 1987Assignee: Imperial Chemical Industries PLCInventor: Arthur Ibbotson
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Patent number: 4695657Abstract: A process for the preparation of compounds containing a difluoromethylene group in a position .alpha. to an oxygen atom. An alcohol or a phenol is brought into contact with trifluoroacetic acid or a halide or anhydride thereof in anhydrous liquid hydrofluoric acid, in the presence of boron trifluoride, in a quantity such that the absolute pressure of boron trifluoride is at least about one bar. The compounds obtained according to the invention are used as synthesis intermediates in the pharmaceutical, plant-protection, and dye industries, as anesthetics and as additives for lubricating oils.Type: GrantFiled: December 17, 1985Date of Patent: September 22, 1987Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Michel Desbois
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Patent number: 4683342Abstract: Described is a process for preparing natural benzaldehyde and acetaldehyde and compositions of matter containing natural benzaldehyde and acetaldehyde as well as products produced thereby and organoleptic utilities thereof, which process comprises the step of contacting with base naturally occurring cinnamaldehyde or a natural product rich in cinnemaldehyde such as Ceylon oil of cinnamon, Ceylon cinnamon bark, Saigon cinnamon bark, cassia oil, Ceylon cinnamon quills, Cinnamon leaf oil, oil of cinnamon Madagascar or the like according to the reaction: ##STR1## the reaction taking place in aqueous media and in the presence of a food grade or natural nonionic emulisifier, preferably a nonionic sorbitan derivative emulsifying agent and in the absence of any other reagents.Type: GrantFiled: August 13, 1986Date of Patent: July 28, 1987Assignee: International Flavors & Fragrances Inc.Inventors: Alan O. Pittet, Ranya Muralidhara, Arthur L. Liberman
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Patent number: 4673766Abstract: A method is disclosed for producing benzaldehyde by fractionally steam distilling benzaldehyde from cinnamaldehyde in the presence of hydroxide catalyst and at a pH on the order of about 11 to about 13. Conversions of cinnamaldehyde to benzaldehyde can be achieved on the order of about 75% or more.Type: GrantFiled: April 25, 1986Date of Patent: June 16, 1987Assignee: Mallinckrodt, Inc.Inventors: Keith T. Buck, Anthony J. Boeing, Joseph E. Dolfini
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Patent number: 4638096Abstract: A process is disclosed for preparing hydroxyarylaldehydes wherein a corresponding phenolic compound is reacted with formaldehyde, in the presence of a titanium or zirconium containing catalyst, optionally in the presence of a catalyst promoter. Among other uses, the aldehydes are particularly useful as intermediates in the preparation of the corresponding oximes, which find utility as metal extractants.Type: GrantFiled: October 12, 1982Date of Patent: January 20, 1987Assignee: Henkel CorporationInventor: Michael J. Virnig
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Patent number: 4617405Abstract: Alpha, beta carbonyl compounds are prepared from an acid anhydride selected from the group consisting of glutaric anhydride and 3-alkyl glutaric anhydride, and a beta-hydroxy carbonyl compound having the following chemical formula:R.sub.2 COH--CHR--CRO or R.sub.2 COH--CHR--CNwhere each R is any substitutent group.The process comprises: (a) reacting the acid anhydride and the beta-hydroxy carbonyl compound in the presence of a catalytically effective amount of an acid catalyst to form an ester; (b) reacting the ester in the presence of a catalytically effective amount of a base catalyst to form a alpha, beta-unsaturated carbonyl compound and a carboxylic acid; and (c) separating the alpha, beta-unsaturated carbonyl compound and the carboxylic acid.Type: GrantFiled: September 25, 1984Date of Patent: October 14, 1986Assignee: A. E. Staley Manufacturing CompanyInventors: Donald E. Kiely, Martin Seidman
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Patent number: 4605778Abstract: The present invention relates to novel musk compounds, useful as fragrance materials which have the structure: ##STR1## wherein R is hydrogen or methyl and R.sub.1 and R.sub.2 are hydrogen, methyl, or ethyl, and provides methods for preparing these compounds from readily available intermediates. The invention also provides fragrance compositions which include the compounds, and processes for altering the organoleptic properties of perfume compositions, colognes and perfumed articles by adding organoleptically effective amounts of the compounds.Type: GrantFiled: June 6, 1984Date of Patent: August 12, 1986Assignee: Fritzsche Dodge & Olcott Inc.Inventors: Brian J. Willis, Teodosij Zazula
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Patent number: 4604243Abstract: An olefin, especially an activated olefin, is arylated by reaction with an arylamine, such as an aniline, in an inert polar organic solvent and in the presence of an alkyl nitrite, a hydrogen halide, and a catalytic amount of a copper catalyst having the copper in an oxidation state below +2.Type: GrantFiled: July 25, 1985Date of Patent: August 5, 1986Assignee: Ethyl CorporationInventor: Robert I. Davidson
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Patent number: 4599457Abstract: An improvement in the process for preparing hydroxyarylaldehydes is disclosed where a phenolic compound is reacted with formaldehyde, in the presence of a catalyst such as a titanium or zirconium containing catalyst, optionally in the presence of a catalyst promoter, wherein the improvement is the addition of a yield effective amount of a modifier having the formula: ##STR1## where R.sub.1 is selected from the group consisting of: an alkyl group having from 1 to 12 carbon atoms, a cycloalkyl group that can have 5 and 6 carbon atoms, and an H, and where R.sub.2 is selected from the group consisting of: an alkyl group having from 1 to 12 carbon atoms, and a cyclo alkyl group that can have 5 to 6 carbon atoms; and where R.sub.1 and R.sub.2 can together form a cyclic group that can have 5 and 6 carbon atoms.Type: GrantFiled: March 20, 1985Date of Patent: July 8, 1986Assignee: Henkel CorporationInventors: Phillip L. Mattison, LeRoy Krbechek
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Patent number: 4588835Abstract: A process for preparing an alkoxyphenol represented by the formula: ##STR1## wherein R is hydrogen, alkyl having 1 to 4 carbon atoms, formyl, hydroxymethyl, alkoxymethyl, dialkoxymethyl, acetoxymethyl or diacetoxymethyl, R' is alkyl having 1 to 4 carbon atoms, and n is an integer of 1 to 5, characterized in that a phenol halide represented by the formula: ##STR2## wherein R and n are as defined above, and X is chlorine or bromine is reacted, in the presence of a copper salt serving as a catalyst and of a solvent, with a product prepared by heating, in the presence of a dehydrating agent, an alkali metal hydroxide and a compound of the formula R'OH wherein R' is as defined above.Type: GrantFiled: October 19, 1984Date of Patent: May 13, 1986Assignee: Otsuka Kagaku Yakuhin Kabushiki KaishaInventors: Sigeru Torii, Hideo Tanaka, Mitsuo Akada
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Patent number: 4585898Abstract: 3-Bromobenzaldehydes are prepared by reacting a benzaldehyde having a free 3-position with bromine chloride in the presence of aluminum chloride and a small amount of dibromomethane.Type: GrantFiled: December 18, 1984Date of Patent: April 29, 1986Assignee: Hardwicke Chemical CompanyInventors: Roland L. Lau, John S. Hudson
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Patent number: 4579975Abstract: Stilbene-4,4'-dialdehyde can be produced by reaction of ethylene with 4-bromobenzaldehyde in the presence of a base and of a palladium compound as catalyst in a simple and economical manner in high yields, by performing the reaction under a partial pressure of ethylene of 0.01 to 1 bar. The stilbene-4,4'-dialdehyde obtained is suitable for example for producing optical brighteners.Type: GrantFiled: March 13, 1985Date of Patent: April 1, 1986Assignee: Ciba-Geigy CorporationInventors: Dieter Reinehr, Alwyn Spencer
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Patent number: 4568772Abstract: This invention discloses a novel process for producing p-t-butyl-.alpha.-methyldihydrocinnamaldehyde which comprises converting the .alpha.-methyldihydrocinnamaldehyde to an enamine, oxazolidine or a Schiff's base, reacting said derivative with a tertiary butyl cation, and then removing the protective group.Type: GrantFiled: September 14, 1983Date of Patent: February 4, 1986Assignee: Givaudan CorporationInventors: Albert Gabbai, Karl-Fred De Polo
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Patent number: 4564712Abstract: Diphenyl ethers are prepared by Ullmann reaction of alkali metal phenolates with halobenzenes in the presence of basic copper carbonate and/or copper salts of lower aliphatic carboxylic acids as catalysts. These special catalysts have a better catalytic activity than other copper catalysts known for the Ullmann reaction.The diphenyl ethers prepared or obtainable according to the invention are mainly intermediates in diverse fields such as pharmaceuticals or plant protecting agents.Type: GrantFiled: November 23, 1983Date of Patent: January 14, 1986Assignee: Hoechst AktiengesellschaftInventors: Herbert Kuckertz, Georg Schaeffer
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Patent number: 4556743Abstract: A process is disclosed for selectively decarbonylating a compound of the formula ##STR1## in a mixture containing I and a compound of the formula ##STR2## wherein R is hydrogen or at least one lower alkyl group and R.sup.1 is hydrogen or a lower alkyl group. In such a process, the mixture is treated with a catalytically effective amount of a palladium catalyst to selectively decarbonylate the compound of formula I therein and the compound of formula II is recovered from the treated mixture.Type: GrantFiled: July 2, 1984Date of Patent: December 3, 1985Assignee: Chem-Fleur International, Inc.Inventors: James E. McKenna, Thomas Plocek
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Patent number: 4551558Abstract: Substituted bromobenzaldehydes, e.g., 5-bromovanillin, are facilely prepared with overall avoidance of HBr by-product, by (i) first brominating the corresponding benzaldehyde with a less than stoichiometric amount of bromine, and (ii) completing said bromination reaction with a brominating couple which comprises (1) the hydrobromic acid generated in situ in the step (i) and (2) a bromide ion oxidizer.Type: GrantFiled: December 24, 1984Date of Patent: November 5, 1985Assignee: Rhone-Poulenc Specialites ChimiquesInventors: Serge Ratton, Jean-Luc Bougeois
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Patent number: 4551557Abstract: Substituted bromobenzaldehydes, e.g., 5-bromovanillin, are facilely prepared without conjoint production of HBr, by brominating the corresponding benzaldehydes with a brominating agent couple which comprises hydrobromic acid and a bromide ion oxidizer.Type: GrantFiled: December 24, 1984Date of Patent: November 5, 1985Assignee: Rhone-Poulenc Specialites ChimiquesInventors: Serge Ratton, Jean-Luc Bougeois
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Patent number: 4542233Abstract: Improvement in the process for preparing biaryl compounds via coupling of an arylamine with an arene in the presence of a nitrite, an acid and copper metal or a derivative thereof; the improvement is consisting in adding to the reaction mixture a trialkylorthoformate. The process may be used for preparing drugs such as Flurbiprofen and Xenbucin or intermediate compounds particularly useful for preparing Flurbiprofen, Flufenisal, Chlordimorin, Xenbucin, Xenysalate, Xenyhexenic acid and the like.Type: GrantFiled: July 20, 1983Date of Patent: September 17, 1985Assignee: Biaschim S.p.A.Inventors: Oreste Piccolo, Aldo Belli, Giovanni Villa, Enrico Zen, Attilio Citterio
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Patent number: 4540828Abstract: Catalysts and a method of using said catalysts for the alkoxylation of a variety of materials is disclosed. Catalysts so described produce alkoxylates having a very sharp alkoxylate distribution. The catalysts are supported and unsupported dialkoxy and dialkyl metal fluorides and halides and alkyl metal difluorides and dihalides.Type: GrantFiled: February 25, 1983Date of Patent: September 10, 1985Assignee: Vista Chemical CompanyInventor: Kang Yang
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Patent number: 4523037Abstract: By reacting, using as a catalyst a modified or unmodified cyclodextrin, a phenol compound with a haloform in the presence of an alkali metal hydroxide, while maintaining the molar ratio of the cyclodextrin to the haloform at 0.5 to 10, a substituent group derived from the haloform can be introduced to the para-position of the phenol compound with high selectivity, whereby useful para-substituted phenol derivatives can be advantageously obtained.Type: GrantFiled: September 7, 1983Date of Patent: June 11, 1985Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Hidefumi Hirai, Makoto Komiyama
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Patent number: 4515987Abstract: Described is a genus of compounds defined according to the structure: ##STR1## (Z) represents one of the moieties ##STR2## as well as the substantially pure compound defined according to the structure: ##STR3## and the use thereof for augmenting or enhancing the aroma or taste of consumable materials including foodstuffs, chewing gums, medicinal products, toothpastes, chewing tobaccos, smoking tobaccos, smoking tobacco articles, perfumes, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softeners, fabric softener articles, perfumed articles, hair preparations and the like.Type: GrantFiled: June 26, 1984Date of Patent: May 7, 1985Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, Theodore J. Tyszkiewicz, Michael Licciardello, Manfred H. Vock, Joaquin F. Vinals, Patrick Whalen, Marie R. Hanna
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Patent number: 4507492Abstract: Allyl derivatives of phenols, thiophenols and arylamines are prepared by contacting such aromatic reactant with an allyl lower alkyl carbonate in the presence of a molybdenum, tungsten or Group VIII metal.Type: GrantFiled: May 6, 1983Date of Patent: March 26, 1985Assignee: The Dow Chemical CompanyInventor: Edmund P. Woo
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Patent number: 4504671Abstract: Aldoxime or ketoxime-O-alkanoic acid is prepared by transoximation of an aldehyde or ketone, the reaction being conducted in a liquid phase at a pressure below one atmosphere. Conversion of the aldoxime or ketoxime-O-alkanoic acid to the ester or salt form is also described.Type: GrantFiled: October 15, 1982Date of Patent: March 12, 1985Assignee: PPG Industries, Inc.Inventors: Dennis K. Krass, John C. Crano, Melvin S. Newman
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Patent number: 4500738Abstract: Alkoxymethyl protecting groups for organic hydroxyl substituents may be introduced into the desired compounds by acetal exchange between an alkylal and an alcohol in the presence of phosphorus oxychloride and dimethylformamide.Type: GrantFiled: December 8, 1983Date of Patent: February 19, 1985Assignee: American Home Products CorporationInventor: Henry G. Schouten
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Patent number: 4495353Abstract: The invention relates to a process for substituting for a halogen atom attached to the nuclear carbon atom of an aromatic ring, a substituent of the formula -O-R wherein R represents alkyl, alkenyl, alkynyl or benzyl, which process comprises reacting the halogen-substituted aromatic compound with an alcoholate of the formula M.sup.n+ [O--R].sub.n.sup..crclbar. wherein M is an alkali metal atom or alkaline earth metal atom, n is the valency of M, and R is as defined above, in the presence of an active catalyst mixture comprising (i) a formic acid ester of an organic alcohol having the formula R.sup.2 --O--CO--H wherein R.sup.2 is as defined for R above; and (ii) a cuprous salt; in a liquid medium which is a solvent for the catalyst mixture and in which the halogen-substituted aromatic compound is at least partially soluble, under substantially anhydrous conditions and a non-oxidizing atmosphere. The invention further relates to a catalyst used in the above process.Type: GrantFiled: June 13, 1983Date of Patent: January 22, 1985Assignee: Sterling Drug Inc.Inventor: Robert J. Bryant
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Patent number: 4487975Abstract: Phenols, including the polyhydric phenols, are selectively monoetherified with an alkyl or alkenyl carboxylate, or admixture of compounds adapted to in situ form such carboxylate, in the presence of a salt of a carboxylic acid.Type: GrantFiled: August 11, 1982Date of Patent: December 11, 1984Assignee: Rhone-Poulenc IndustriesInventor: Serge Ratton
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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: 4471126Abstract: There is a method for the production of 3-phenylpyrrole derivatives having the general formula ##STR1## wherein X is halogen, nitro or haloalkyl having 1 to 3 carbon atoms;n is 0, 1 or 2; andZ is hydrogen or halogen;which comprises reacting a compound having the general formula ##STR2## wherein X and n are as previously defined; andY is hydrogen or halogen;with ammonia or aqueous ammonia in an organic solvent.A compound having the general formula [I] is useful as fungicide or intermediate thereof.Type: GrantFiled: April 18, 1983Date of Patent: September 11, 1984Assignee: Nippon Soda Company LimitedInventors: Akiyoshi Ueda, Humihiko Nagasaki, Yutaka Takakura, Shigeru Kojima
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Patent number: 4465864Abstract: An aromatic compound is hydroxylated by reacting the aromatic compound in an aqueous solvent with a triiodide salt to form a reaction mixture containing the corresponding iodoaromatic compound. The mixture is reacted, without separating the iodoaromatic compound, with a hydroxylating agent to form the corresponding hydroxy aromatic compound. The iodide salt, formed as a by-product of the reaction, is then separated for reuse in the process.Type: GrantFiled: August 2, 1982Date of Patent: August 14, 1984Assignee: International Telephone and Telegraph CorporationInventors: Geoffrey K. Cooper, Lewis G. Harruff
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Patent number: 4453018Abstract: An alkylated phenolic ether is prepared by reacting in the absence of a protic solvent a phenolic compound containing an unreacted phenolic hydroxy group with an alkyl sulfite of the formula (RO).sub.2 SO in which R is a one to four carbon alkyl group, the reaction occurring in one step and without the intermediate preparation of a phenolate.Type: GrantFiled: April 1, 1982Date of Patent: June 5, 1984Assignee: International Telephone and Telegraph CorporationInventor: Randall B. Nelson
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Patent number: 4453017Abstract: A methylated phenolic ether is prepared by reacting in the absence of a protic solvent a phenolic compound containing an unreacted phenolic hydroxy group with trimethyl phosphate, the reaction occurring in one step and without the intermediate preparation of a phenolate.Type: GrantFiled: April 1, 1982Date of Patent: June 5, 1984Assignee: International Telephone and Telegraph CorporationInventor: Randall B. Nelson
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Patent number: 4453004Abstract: A process for the preparation of an alkylated phenolic ether comprising reacting a phenolic compound at a temperature of at least the melting point of the phenol and in the absence of a solvent with an alkylating agent until an alkylated phenol is produced.Type: GrantFiled: April 1, 1982Date of Patent: June 5, 1984Assignee: International Telephone and Telegraph CorporationInventor: Randall B. Nelson
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Patent number: 4446075Abstract: Substituted bromofluorobenzene, wherein the fluorine is in para-position and the bromine in meta-position to another substituent, is prepared by direct bromination of the corresponding fluorobenzene derivative. Bromination is advantageously carried out in the presence of a catalyst, preferably a metal or metal salt. The elementary bromine is used in an amount of 0.9 to 1.3 mols per mol of fluorobenzene derivative and the reaction temperature is between 20.degree. and 200.degree. C. The bromofluorobenzene derivatives are suitable for the synthesis of medicaments and plant protective agents.Type: GrantFiled: February 20, 1981Date of Patent: May 1, 1984Assignee: Riedel-de Haen AGInventors: Kurt Eiglmeier, Reinhard Knieps
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Patent number: 4395571Abstract: Racemic mixtures of d,1-2-(6-methoxy-2-naphthyl)propanal are resolved by forming a condensation product with N-R-D-glucamine or a salt thereof where R is hydrogen, alkyl of 1 to 36 carbon atoms or cycloalkyl of 3 to 8 carbon atoms, from which a product substantially enriched in d-2-(6-methoxy-2-naphthyl)propanal can be obtained and then can be selectively oxidized to d-2-(6-methoxy-2-naphthyl)propionic acid.Type: GrantFiled: June 3, 1982Date of Patent: July 26, 1983Assignee: Syntex (U.S.A.) Inc.Inventor: Charles A. Dvorak
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Patent number: 4389527Abstract: This invention discloses a novel process for producing dihydrocinnamaldehyde derivatives which comprises reacting a benzene derivative with an alken-2-ylidene diacylate or an .alpha.-ethylenic aldehyde in trifluoroacetic acid (TFA).Type: GrantFiled: June 30, 1981Date of Patent: June 21, 1983Assignee: Givaudan CorporationInventors: Roy H. Valentine, Harold A. Brandman
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Patent number: 4379026Abstract: A process for the purification in the presence of water of impure benzaldehyde by which a purified benzaldehyde is prepared which has improved color stability and improved olfactory characteristics. The process is comprised of the steps of treating the impure benzaldehyde simultaneously with water and a metal less noble than hydrogen followed by distillation.Type: GrantFiled: January 20, 1982Date of Patent: April 5, 1983Assignee: Stamicarbon, B.V.Inventor: Cornelis Jongsma
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Patent number: 4351962Abstract: A process is provided for the preparation of hydroxy benzene carboxaldehydes having the formula: ##STR1## wherein: R is selected from the group consisting of alkyl, alkoxy, cycloalkyl, aryl, alkoxyalkyl, fluoroalkyl, and hydroxyalkyl oxyalkylene having from one to about twenty carbon atoms; hydroxyalkyl having at least two to about twenty carbon atoms; hydroxy; aldehyde CHO; and halogen;n.sub.1, n.sub.2 and n.sub.3 are zero or 1; and at least one of n.sub.1, n.sub.2 and n.sub.3 is 1; andx is zero, 1, 2, 3 or 4, which comprises:(1) condensing with a formaldehyde compound a phenol having the formula: ##STR2## wherein R is selected from the group consisting of alkyl, alkoxy, hydroxyalkyl, cycloalkyl, aryl, alkoxyalkyl, fluoroalkyl, and hydroxyalkyl oxyalkylene having from one to about twenty carbon atoms; hydroxy; and halogen; andx is zero, 1, 2, 3 or 4,and unsubstituted in at least one ortho or para position in an aqueous reaction medium comprising phenol:HCHO in a molar ratio within the range from about 1:0.Type: GrantFiled: July 11, 1980Date of Patent: September 28, 1982Assignee: Rhone Poulenc Inc.Inventors: Peter S. Gradeff, Stanley T. Murayama
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Patent number: 4350833Abstract: Terephthaldialdehyde monoacetals represented by the general formula: ##STR1## (wherein, R.sub.1 and R.sub.2 are lower alkyl groups) are novel compounds, and they are produced by the reaction of terephthaldialdehyde with alcohols in the presence of a strongly acidic substance as a catalyst.Type: GrantFiled: January 28, 1981Date of Patent: September 21, 1982Inventor: Kunihiro Ichimura
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Patent number: 4346239Abstract: A process for the preparation of 2-methylene aldehydes is disclosed wherein formaldehyde is reacted with an aldehyde of the general formula R--CH.sub.2 CHO, where R stands for a substituted or unsubstituted organic radical having from 2 to 12 carbon atoms. The reaction takes place in the presence of a mixture of a secondary amine and an organic carboxylic acid having up to 5 carbon atoms.Type: GrantFiled: December 29, 1980Date of Patent: August 24, 1982Assignee: Ruhrchemie AGInventors: Hanswilhelm Bach, Eike Brundin, Wilhelm Gick
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Patent number: 4335055Abstract: Compounds of the formula I ##STR1## in which Z, Z.sub.1, R, m and p are as defined in patent claim 1, can be obtained in a simple and economical manner by a novel process wherein a halide of the formula II ##STR2## is reacted with a substituted or unsubstituted vinylbenzene or vinylnaphthalene derivative in the presence of a base and of certain palladium catalysts, such as palladium acetate. The compounds (I) or functional derivatives preparable therefrom are useful, for example, for the preparation of known dyes or fluorescent brighteners, or can be used directly as fluorescent brighteners or as scintillators.Type: GrantFiled: May 8, 1981Date of Patent: June 15, 1982Assignee: Ciba-Geigy CorporationInventors: Hans-Ulrich Blaser, Dieter Reinehr, Alwyn Spencer
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Patent number: 4328363Abstract: Halogen-substituted olefin addition compounds that contain a carbonyl group are formed by oxidatively adducting an olefin and a carbonyl compound such as a ketone, aldehyde, or ester. The method consists of reacting the olefin and the carbonyl component, in solution, with an oxidizing ion of manganese, cerium or vanadium in the presence of fluoride, chloride or bromide ion. This ionic component is incorporated in the adduct and appears on the olefin-derived carbon atom gamma to the carbonyl group. The gamma halogen substituted adducts are readily converted to cyclopropane derivatives, including pyrethroid intermediate compounds.Type: GrantFiled: November 8, 1978Date of Patent: May 4, 1982Assignee: Mobil Oil CorporationInventors: El-Ahmadi I. Heiba, Ralph M. Dessau
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Patent number: 4322563Abstract: Substituted biphenyl-2-carboxaldehydes are prepared in good yield by reacting palladium complexes of substituted benzaldehyde aniline Schiff bases with substituted phenylmagnesium bromides in the presence of at least six, preferably eight, molar equivalents of triphenylphosphine.Type: GrantFiled: February 11, 1981Date of Patent: March 30, 1982Assignee: Merck & Co., Inc.Inventor: William F. Hoffman
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Patent number: 4317933Abstract: 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: November 9, 1977Date of Patent: March 2, 1982Assignee: The Goodyear Tire & Rubber CompanyInventor: Dane K. Parker
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Patent number: 4316989Abstract: A process for preparing difluoromethoxy derivatives of aromatic aldehydes having a common formula ##STR1## where Z is H,H; or n is a whole number of 1 and 2.The above process comprises the reaction between oxy derivatives of aromatic aldehydes selected from the group consisting of monooxy derivatives of aromatic aldehydes, and difluorochloromethane which reaction is carried out in an aqueous-dioxane medium at a temperature of 60.degree. to 70.degree. C., in the presence of 6 to 10 moles of caustic alkali per 1 mole of a starting oxyaldehyde.Type: GrantFiled: May 29, 1980Date of Patent: February 23, 1982Inventors: Jury A. Fialkov, Svetlana V. Shelyazhenko
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Patent number: 4314086Abstract: Aliphatic/aromatic ethers are prepared by reacting an aliphatic halide with either an alkali or alkaline earth metal, or ammonium phenolate or naphtholate, in an inert organic solvent, and in the presence of at least one tertiary amine sequestering agent having the formula:N--CHR.sub.1 CHR.sub.2 --O--CHR.sub.3 --CHR.sub.4 --O--.sub.n R.sub.5 ].sub.Type: GrantFiled: June 20, 1980Date of Patent: February 2, 1982Assignee: Rhone-Poulenc IndustriesInventors: Gerard Soula, Daniel Michelet
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Patent number: 4307034Abstract: An inert organic solvent dispersion of alkali hydroxide is prepared by mixing an alkali hydroxide, an inert organic solvent and a stabilizer and heating and stirring at the temperature for forming the pasty alkali hydroxide and cooling the dispersion. The dispersion of alkali hydroxide is used in a reaction of an active methylene compound with an organoalkyl halide such as a reaction of a halophenylacetonitrile with an isopropyl halide to obtain .alpha.-isopropyl halophenylacetonitrile.Type: GrantFiled: September 13, 1979Date of Patent: December 22, 1981Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Yoshiki Nakayama, Taro Izawa, Yasushi Higuchi, Yutaka Ohishi, Chihiro Yazawa
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Patent number: 4298762Abstract: Improved conversions of primary allylic and benzylic alcohols are obtained in an Oppenauer oxidation process, under Oppenauer oxidation conditions, by carrying out the oxidation employing furfural as the hydrogen acceptor. Primary alcohols to which the present invention relates are allylic alcohols substituted in at least the 2-position with a hydrocarbon radical and benzylic alcohols.Type: GrantFiled: December 5, 1979Date of Patent: November 3, 1981Assignee: SCM CorporationInventors: William J. Ehmann, Walter E. Johnson, Jr.
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Patent number: 4288386Abstract: The Ullman reaction for the preparation of diaryl ethers by coupling aryl halides with metal phenolates is conducted in the presence of at least one tertiary amine sequestering agent having the formula:N--CHR.sub.1 --CHR.sub.2 --O--CHR.sub.3 --CHR.sub.4 --O--.sub.n R.sub.5 ].sub.Type: GrantFiled: May 12, 1980Date of Patent: September 8, 1981Assignee: Rhone-Poulenc IndustriesInventors: Gerard Soula, Louis Linguenheld