Halogen Containing Reactant Patents (Class 568/316)
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Patent number: 5349107Abstract: Disclosed herein is a process for producing a .gamma.-hydroxyketone (2), which comprises asymmetrically hydrogenating a .gamma.-diketone (1) in the presence of a ruthenium-optically active phosphine complex as a catalyst ##STR1## wherein R.sup.1 and R.sup.2 mean individually an alkyl or phenyl group which may have a substituent group. According to the invention, optically active .gamma.-hydroxyketones useful in synthesizing optically active moiety in, biodegradable polymers, perfumes, intermediates for synthesizing medicines and the like can be efficiently prepared.Type: GrantFiled: October 1, 1993Date of Patent: September 20, 1994Assignee: Takasago International CorporationInventors: Seiji Watanabe, Shigeru Mitsuhashi, Hidenori Kumobayashi
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Patent number: 5260489Abstract: A process for purifying a halogenated aromatic sulfone or ketone compound comprises contacting the compound with a mixture containing a solvent having a normal boiling point less than about 225.degree. C. and water to form a second mixture, heating the second mixture at a temperature sufficient to substantially dissolve the halogenated compound to form a third mixture, cooling the third mixture to purify and recrystallize the compound, and recovering the purified, recrystallized compound. A second embodiment of the invention comprises repeating the purification process steps at least once to further purify the halogenated aromatic sulfone or ketone compound.Type: GrantFiled: September 30, 1992Date of Patent: November 9, 1993Assignee: Phillips Petroleum CompanyInventors: Rex L. Robsein, Jimmie J. Straw, Darryl R. Fahey
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Patent number: 5256826Abstract: A process for the preparation of aromatic carbonyl or sulfonyl compounds with a diaryl ether structure by reacting phenols with halogenated carbonyl- or sulfonylaromatic compounds in a dipolar aprotic solvent is carried out in the presence of catalytic amounts of alkali metal nitrite or an aromatic nitro, nitroso, azo, azoxy or hydrazo compound.Type: GrantFiled: August 31, 1992Date of Patent: October 26, 1993Assignee: BASF AktiengesellschaftInventors: Erwin Hahn, Heinrich J. Eilingsfeld, Helmut Reichelt, Alexander Aumueller, Bernd Hupfeld
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Patent number: 5254732Abstract: The invention describes N-fluorosulfonimides which are useful as fluorinating agents. The N-fluorosulfonimides are stable, easily synthesized, and allow the introduction of fluorine into organic compounds under mild conditions.Type: GrantFiled: February 28, 1992Date of Patent: October 19, 1993Assignee: Allied-Signal Inc.Inventor: Edmond Differding
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Patent number: 5250738Abstract: A process for the preparation of 1,4-bis(4-hydroxybenzoyl)benzene of the formula (I) ##STR1## by reacting a 1,4-bis(4-halobenzoyl)benzene of the formula (II) ##STR2## in which X is a fluorine, chlorine or bromine atom, with an alkali metal hydroxide or alkaline earth metal hydroxide or with mixtures of these hydroxides in a solvent which is inert to the reaction components under the reaction conditions at temperatures of about 100.degree. C. to about 250.degree. C., if appropriate in the presence of a phase transfer catalyst.Type: GrantFiled: February 24, 1992Date of Patent: October 5, 1993Assignee: Hoechst AktiengesellschaftInventors: Joachim Hackenbruch, Theodor Papenfuhs
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Patent number: 5235000Abstract: This invention relates to a process for reducing the formation of carbonyl halide in bromine chloride and to an improved process for the bromination of compounds with BrCl in the presence of a carbonyl halide poisonable catalyst.Type: GrantFiled: December 10, 1990Date of Patent: August 10, 1993Assignee: Ethyl CorporationInventor: Bonnie G. McKinnie
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Patent number: 5233054Abstract: Halophthalic anhydrides are prepared by the liquid phase reaction of a brominating agent with halogen substituted hexa- or tetra-hydrophthalic anhydrides.Type: GrantFiled: June 26, 1991Date of Patent: August 3, 1993Assignee: Occidental Chemical CorporationInventors: David Y. Tang, Mary K. Cocoman, Harry E. Buckholtz
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Patent number: 5185454Abstract: Symmetrical diaryl-acetylenes can be prepared by reacting an aryl halide with acetylene in the presence of a palladium catalyst and a base. If the acetylene is introduced into the liquid reaction mixture using a high intensity gas dispersion means, the aryl halide used can be an aryl bromide.Type: GrantFiled: October 2, 1990Date of Patent: February 9, 1993Assignee: Bayer AktiengesellschaftInventors: Axel Bader, Dieter Arlt
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Patent number: 5171893Abstract: This invention concerns a process for preparing fluoroalkyl substituted olefins, fluorinated ketones and fluorinated aromatic compounds by the catalyzed reaction of fluoroalkylsilanes with selected fluorinated olefins, acyl fluorides and fluorinated aromatic compounds, respectively.Type: GrantFiled: December 2, 1991Date of Patent: December 15, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventor: William B. Farnham
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Patent number: 5169958Abstract: A process for the preparation of .alpha.,.beta.-unsaturated carbonyl compounds of the formula I ##STR1## where R.sup.1 is hydrogen, C.sub.1 -C.sub.10 -alkyl, C.sub.1 -C.sub.10 -alkoxy or aryloxy,R.sup.2 is aryl which is unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, trifluoromethyl and/or halogen andR.sup.3 is tetrahydrofuranyl or aryl which is substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, trifluoromethyl and/or halogen, which comprises reacting 3-amino-2-propen-1-ones of the formula II ##STR2## where R.sup.1 and R.sup.2 have the abovementioned meanings, and R.sup.4 and R.sup.5 are, independently of one another, hydrogen, C.sub.1 -C.sub.10 -alkyl or aryl, with a magnesium halide of the formula IIIR.sup.3 --Mg--Y (III)where Y is halogen, at from -20.degree. to 100.degree. C., and novel .alpha.,.beta.-unsaturated carbonyl compounds and novel 3-amino-2-propen-1-ones are described.Type: GrantFiled: October 1, 1991Date of Patent: December 8, 1992Assignee: BASF AktiengesellschaftInventors: Heinz Isak, Norbert Goetz, Thomas Kuekenhoehner
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Patent number: 5138107Abstract: A process is disclosed for chlorinating, brominating and/or iodinating an organic substrate containing both a single acidic hydrogen atom and at least one electron withdrawing group attached to the same carbon atom. The process replaces the single acidic hydrogen with chlorine, bromine and/or iodine and involves reacting the substrate in solution with a halogenating agent (e.g., a perhalomethane wherein the halogen substituents are I, Br and/or Cl, a trihaloacetic acid ester wherein the halogen substituents are Br and/or Cl, or a perfluoroalkyl halide wherein the halide is I, Br and/or Cl) in the presence of (i) a phase transfer catalyst of the formula R.sup.1 R.sup.2 R.sup.3 R.sup.4 LJ where L is selected from the group consisting of phosphorus and nitrogen, where J is an inorganic anion other than fluoride, and where R.sup.1, R.sup.2, R.sup.3 and R.sup.Type: GrantFiled: July 12, 1991Date of Patent: August 11, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventor: Yoel Sasson
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Patent number: 5136081Abstract: The invention provides a process for the preparation of fungicidally active cyclopentene derivatives of the general formula ##STR1## cyclopentane derivatives of the general formula ##STR2## and cyclohexane derivatives of the general formula ##STR3## in which n, R, R.sup.1, R.sup.2, R.sup.5, X and Y are as herein defined. Compounds of formula II and III are also provided which are useful as intermediates in the preparation of certain fungicidally active cyclopentane derivatives.Type: GrantFiled: September 11, 1989Date of Patent: August 4, 1992Assignee: Shell Internationale Research Maatschappij B.V.Inventor: Paul H. Briner
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Patent number: 5132475Abstract: A process is disclosed for chlorinating, brominating and/or iodinating an organic substrate containing both a single acidic hydrogen atom and at least one electron withdrawing group attached to the same carbon atom. The process replaces the single acidic hydrogen with chlorine, bromine and/or iodine and involves reacting the substrate in solution with a halogenating agent (e.g., a perhalomethane wherein the halogen substituents are I, Br and/or Cl, a trihaloacetic acid ester wherein the halogen substituents are Br and/or Cl, or a perfluoroalkyl halide wherein the halide is I, Br and/or Cl) in the presence of a quaternary ammonium fluoride catalyst of the formula R.sup.1 R.sup.2 R.sup.3 R.sup.4 NF where R.sup.1, R.sup.2, and R.sup.3 and R.sup.4 are independently chosen from the group consisting of hydrocarbyl radicals containing from 1 to about 20 carbon atoms.Type: GrantFiled: July 12, 1991Date of Patent: July 21, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventor: Yoel Sasson
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Patent number: 5118839Abstract: A process for preparing nitro substituted polyarylketones of the formula: ##STR1## is disclosed. The process involves the condensation of ##STR2## where R.sub.A is hydrogen, --COOH, or C.sup.1 to C.sub.12 linear or branched alkyl, Y and Y' are the same or different and are a chemical bond ##STR3## or --Si(CH.sub.3).sub.2 -- and m is 0 or 1 and X is halo. These nitro groups of these compounds can be reduced to provide the corresponding amines, which are useful for the preparation of thermally stable high melting polyimides.Type: GrantFiled: September 4, 1990Date of Patent: June 2, 1992Assignee: Ethyl CorporationInventors: Allan A. Eisenbraun, Venkataraman Ramachandran
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Patent number: 5107029Abstract: This invention concerns a process for preparing diketones and keto-acids by reacting a dicarboxylic acid and an aromatic compound in the presence of an alkylsulfonic acid such as methanesulfonic acid and an organic anhydride compound such as methanesulfonic anhydride or trifluoroacetic anhydride. The diketones and keto-acids can be used to prepare polyketones which are useful as molding plastics, coatings, films, fibers, and the like.Type: GrantFiled: July 23, 1990Date of Patent: April 21, 1992Assignee: Eastman Kodak CompanyInventors: Theodore R. Walker, Jr., Winston J. Jackson, Jr., Jean C. Fleischer
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Patent number: 5026918Abstract: 2,3,5-trisubstituted-2-cyclopentenones or 2,3-disubstituted-2-cyclopentenones (such as cis-jasmone) are prepared by contacting a 3-chloro-3,4-disubstituted-4-pentene-2-one with a strong base. Methods of preparing the reactants are also disclosed.Type: GrantFiled: April 27, 1990Date of Patent: June 25, 1991Assignee: Petrolite CorporationInventor: Jacob Mathew
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Patent number: 5008425Abstract: A process which comprises reacting under substantially anhydrous conditions a perfluoroalkyltrihydrocarbylsilane and a carbonyl compound in the presence of a catalyst such that the carbonyl compound is perfluoroalkylated.Type: GrantFiled: April 12, 1989Date of Patent: April 16, 1991Assignee: Ethyl CorporationInventor: G. Patrick Stahly
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Patent number: 4992591Abstract: A method for producing a compound of the formula ##STR1## wherein: R.sup.1, R.sup.11 and R.sup.12 may be the same or different and each is hydrogen or alkyl;Q is methylene, --O-- or --S--;m and n are independently variable and may each have a value of 0, 1 or 2;X is hydrogen, halo, alkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, hydroxy, alkoxy or trifluoromethyl;Y is hydrogen, hydroxy, alkoxy, ##STR2## --N(R.sup.1).sub.2, ##STR3## where R.sup.1 is as defined above; ring t represents a fused thiophene or fused benzene ring, said fused benzene ring optionally being substituted with a substituent Z as defined below; andZ is X as defined above, amino, alkylamino or ##STR4## {wherein R.sup.10 is hydrogen, alkyl or aryl}, comprising reacting a compound of formula II or formula III ##STR5## with a compound of the formula where Hal is a halogen; andR.sup.13 is acetyl, or Si(R.sup.14).sub.3 where each R.sup.14 independently is alkyl or aryl is disclosed.Type: GrantFiled: December 21, 1989Date of Patent: February 12, 1991Assignee: Schering CorporationInventors: Donald Hou, Janet L. Mas
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Patent number: 4992577Abstract: A process for preparing a compound of the formula ##STR1## in which Y is halogen, alkyl or cycloalkyl optionally substituted by halogen or C.sub.1-4 -alkoxy, alkenyl optionally substituted by halogen, aryl, heteroaryl or alkoxycarbonyl,X is hydrogen, halogen or optionally halogen-substituted alkyl, orX and Y, together with the adjacent C atom, form a saturated cycloalkphatic ring having up to 6 C atoms, andR is hydrogen or C.sub.1 -C.sub.4 -alkyl, comprising reacting an aldehyde of the formula ##STR2## with 2-methylbutan-3-one of the formula ##STR3## in the presence of a hydrohalic acid thereby to form a 4,4-dimethyl-3-halogeno-1-hexen-5-one of the formula ##STR4## in which Hal is halogen, halogenating said compound to produce a compound of the formula ##STR5## and reacting said compound with a base of the formulaR--OM (VI)in whichM is one equivalent of an alkali or alkaline earth metal ion.Compounds IV and V are new. By suitable conditions the trans isomer is selectively produced.Type: GrantFiled: May 22, 1989Date of Patent: February 12, 1991Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Dieter Arlt, Manfred Jautelat
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Patent number: 4978798Abstract: Disclosed is a method of making a bisphenyl dihalomethane by reacting a trihalomethylbenzene with a halobenzene and a Lewis acid. The bisphenyl dihalomethane can than be reacted with water to form a halobenzophenone. In an optical third step ring chlorines that are present can be replaced with fluorines and, in a final step, any remaining chlorines can be removed to leave a fluorobenzophenone. The process is particularly useful in making 4,4'-difluorobenzophenone, which is in turn useful in making polyetheretherketones.Type: GrantFiled: November 13, 1989Date of Patent: December 18, 1990Assignee: Occidental Chemical CorporationInventor: Jeffrey S. Stults
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Patent number: 4973756Abstract: An alpha-hydroxyl-alpha,alpha-di(inert-substituted)-gamma',delta'-yne ketone can be prepared by a procedure comprising contacting an acetylenic Grignard reagent with an alpha-hydroxyl-alpha,alpha-di(inert substituted)-alpha',beta'-ene ketone, and the alpha-hydroxyl-alpha,alpha-di(inert-substituted)-alpha',beta'-ene ketone can be prepared by a procedure comprising steps of contacting, first, an alkoxy allene with a lithium donating organic agent, second, product of the first step with a di(inert-substituted)ketone, and third, product of the second step with an acidic substance.Type: GrantFiled: August 21, 1989Date of Patent: November 27, 1990Assignee: Marion Laboratories, Inc.Inventors: Hans Wynberg, Wolter T. Hoeve, Gerrit A. Barf, Johannes N. Koek, David R. Borcherding
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Patent number: 4956505Abstract: 4,4-Dimethyl-1-(p-chlorophenyl)pentan-3-one can be prepared by condensation of pinacolone and p-chlorobenzaldehyde in an alcohol as solvent in the presence of an inorganic base and by subsequent hydrogenation, in which the reaction mixture obtained in the condensation is hydrogenated directly without isolation of the intermediate 4,4-dimethyl-1-(p-chlorophenyl)-1-penten-3-one after the addition of a hydrogenation catalyst at elevated temperature and superatmospheric pressure to give 4,4-dimethyl-1-(p-chlorophenyl)pentan-3-one, after the hydrogenation catalyst has been separated off from the liquid hydrogenation mixture, the alcohol is largely distilled off, and the water content of the bottom product of the distillation is adjusted in such a manner that it separates into an aqueous and an organic phase, and the 4,4-dimethyl-1-(p-chlorophenyl)pentan-3-one is recovered from the organic phase.Type: GrantFiled: July 5, 1989Date of Patent: September 11, 1990Assignee: Bayer AktiengesellschaftInventors: Franz-Josef Mais, Helmut Fiege, Karl-Wilhelm Henneke
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Patent number: 4912220Abstract: Nitroaryl carbonyl Formula (IIA) compounds, their nitrodihydroaryl carbonyl Formula (I) intermediates, processes for preparing Formula (II) compounds, and a process for preparing Formula (I) compounds, wherein each process comprises the reaction of a nitroaryl compound with a silane.Type: GrantFiled: February 3, 1988Date of Patent: March 27, 1990Assignee: E. I. Du Pont de Nemours and CompanyInventor: Thaliyil V. Rajanbabu
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Patent number: 4912262Abstract: According to the present invention there is provided process for preparing a compound of formula (I): ##STR1## or a salt, acylate or sulphonate derivative thereof; wherein R.sup.1 is an optionally substituted aryl group, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are selected from hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkanoyl or --CO.sub.2 R.sup.a wherein R.sup.a is C.sub.1-4 alkyl or R.sup.2 and R.sup.3 or R.sup.4 and R.sup.5 together with the carbon atom to which they are attached form a C.sub.3-6 cycloalkyl ring, provided that at least R.sub.2 and R.sup.3 or R.sup.4 and R.sup.5 are not both hydrogen and that not more than two of R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are C.sub.1-4 alkanoyl or --CO.sub.2 R.sup.a ; which process comprises reacting a compound of formula (II): ##STR2## wherein R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are as defined in relation to formula (I) with a compound of formula (III):R.sup.1 COCN (III)wherein R.sup.Type: GrantFiled: March 7, 1988Date of Patent: March 27, 1990Assignee: Imperial Chemical Industries PLCInventor: Glynn Mitchell
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Patent number: 4908481Abstract: A simple process for preparing 1-(4-hydroxy-phenyl)-butan-3-one, a sought-after natural aromatic, in a pure form and in good yield from easily accessible starting materials, wherein a 4-tert-alkoxy-benzaldehyde is condensed, under alkaline conditions, to give a novel 1-(4-tert.-alkoxy-phenyl)-but-1-en-3-one, the latter is hydrogenated, during or after this condensation, to give a novel 1-(4-tert.-alkoxy-phenyl)-butan-3-one, and isobutene or 2-methyl-but-1(2)-ene is eliminated from this compound in the presence of a catalytic amount of an acid. The novel intermediates have the general formula ##STR1## where R is H or CH.sub.3 and the broken line may or may not be an additional carbon-carbon bond.Type: GrantFiled: November 18, 1985Date of Patent: March 13, 1990Assignee: BASF AktiengesellschaftInventors: Werner Hoffmann, Dieter Degner
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Patent number: 4871873Abstract: A process for producing arylglyoxal arylimine intermediates, by the DMSO/HBr oxidation of arylmethylketones. The imine compounds are intermediates in the synthesis of carbapenem antibiotics, i.e. imipenem.Type: GrantFiled: March 18, 1988Date of Patent: October 3, 1989Assignee: Merck & Company IncorporatedInventors: Richard Desmond, Sander G. Mills, Ralph P. Volante, Ichiro Shinkai
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Patent number: 4871877Abstract: Quinones may be perfluoroalkylated by means of perfluoroalkyltrihydrocarbyl silane using certain active alkali metal salt catalysts and a proton source. The reaction--which is conducted, preferably in a suitable liquid phase reaction medium, most preferably a dipolar aprotic solvent--results in the formation of gem-disubstituted cyclohexadienones in which the gem substitutes are a perfluoroalkyl group and a hydroxyl group. These gem-disubstituted compounds in turn can be readily converted to perfluoroalkyl substituted aromatics, thus circumventing the traditional need for photochlorination followed by halogen exchange using hydrogen fluoride as a means of preparing perfluoroalkyl aromatic compounds.Type: GrantFiled: May 20, 1988Date of Patent: October 3, 1989Assignee: Ethyl CorporationInventor: G. Patrick Stahly
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Patent number: 4845301Abstract: A process for the preparation of .alpha.-hydroxyketones ##STR1## having a high purity in a good yield from a compound ##STR2## by rearrangement reaction in aqueous alkaline solution, where R.sub.1 and R.sub.3 each represent an alkyl, alkenyl or aryl group, R.sub.2 represents a hydrogen atom or an alkyl, alkenyl or aryl group, and X represents hydroxyl group or a halogen atom.Type: GrantFiled: September 8, 1987Date of Patent: July 4, 1989Assignee: Daicel Chemical Industries, Ltd.Inventors: Kazuo Sato, Noritsugu Yamasaki, Ichirou Takase
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Patent number: 4743690Abstract: Nitroaryl carbonyl Formula (IIA) compounds, their nitrodihydroaryl carbonyl Formula (I) intermediates, processes for preparing Formula (II) compounds, and a process for preparing Formula (I) compounds, wherein each process comprises the reaction of a nitroaryl compound with a silane.Type: GrantFiled: January 16, 1987Date of Patent: May 10, 1988Assignee: E. I. Du Pont de Nemours and CompanyInventor: Thaliyil V. Rajanbabu
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Patent number: 4740624Abstract: Ketones of the formula II ##STR1## with Ar, R.sup.1 and R.sup.2 as indicated below, can be hydroxylated, readily and in high yields, in the .alpha.-position using tetrahalogenomethanes and alkali metal hydroxides under phase-transfer conditions.Type: GrantFiled: April 7, 1986Date of Patent: April 26, 1988Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Manfred Kohler, Michael Romer, Claus P. Herz
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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: 4704475Abstract: A process is provided for preparing 3-hydroxy-3-phenyl-butan-2-one, useful in the preparation of acifran, in high yields by reacting 2,3-butanedione with the appropriate Grignard reagent at low temperature in tetrahydrofuran or admixtures thereof with toluene.Type: GrantFiled: June 2, 1986Date of Patent: November 3, 1987Assignee: American Home Products Corporation (Del.)Inventors: James S. Farina, Corbin L. Cummings
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Patent number: 4691058Abstract: The invention relates to a novel process for producing compounds of the formula I ##STR1## in which R.sup.1 is for example phenyl, and R.sup.2 and R.sup.3 are for example cyclohexyl. With application of the phase-transfer catalysis method, a corresponding compound of the formula II ##STR2## is reacted, in the presence of water, with hydroxide ions, especially with alkali metal hydroxide or alkaline-earth metal hydroxide.Type: GrantFiled: February 14, 1985Date of Patent: September 1, 1987Assignee: Ciba-Geigy CorporationInventor: Werner Stegmann
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Patent number: 4681952Abstract: A process for the preparation of 2,2-dimethyl-3-arylcyclopropanecarboxylic acid or ester of the formula ##STR1## in which Ar is naphthyl or the radical ##STR2## R.sup.1 is H or C.sub.1 -C.sub.4 -alkyl, Z is oxygen, sulphur, or 1,2-ethenediyl, andR.sup.2 represents hydrogen, halogen, cyano, nitro or trialkylsilyl or a radical, which is optionally substituted by halogen, from the series comprising alkyl, cycloalkyl, alkenyl, alkoxy, alkylenedioxy, alkylthio, alkylsulphinyl, alkylsulphonyl, dialkylamino, phenyl and phenoxy,comprising reacting a 1-aryl-1-halogeno-2,2-dimethyl-3-butanone of the formula ##STR3## in which X.sup.1 is chlorine or bromine, with a base in the presence of a diluent at a temperature between about -20.degree. and +150.degree. C., thereby to form a 2,2-dimethyl-3-arylcyclobutanone of the formula ##STR4## and reacting such 2,2-dimethyl-3-arylcyclobutanone with chlorine or bromine in the presence of an inert diluent at a temperature between about -30.degree. and +50.degree. C.Type: GrantFiled: November 7, 1984Date of Patent: July 21, 1987Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Dieter Arlt, Manfred Jautelat
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Patent number: 4675448Abstract: 1-[2,5-Bis(2,2,2-trifluoroethoxy)phenyl]ethanone is chlorinated to 1-[2,5-bis(2,2,2-trifluoroethoxy)phenyl]-2,2-dichloroethanone and, if desired, to 1-[2,5-bis(2,2,2-trifluoroethoxy)phenyl]-2,2,2-trichloroethanone in a solvent mixture of about 0.5-35 parts by volume of 1,2-dichloroethane and one part by volume of acetic acid. The products can then be converted to flecainide. In a preferred embodiment of the invention, the starting material is a crude, wet material that is prepared with a minimum of solids handling.Type: GrantFiled: April 7, 1986Date of Patent: June 23, 1987Assignee: Ethyl CorporationInventor: Barbara C. Stahly
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Patent number: 4659862Abstract: Nitroaryl carbonyl Formula (IIA) compounds, their nitrodihydroaryl carbonyl Formula (I) intermediates, processes for preparing Formula (II) compounds, and a process for preparing Formula (I) compounds, wherein each process comprises the reaction of a nitroaryl compound with a silane.Type: GrantFiled: May 3, 1984Date of Patent: April 21, 1987Assignee: E. I. Du Pont de Nemours and CompanyInventor: Thaliyil V. Rajanbabu
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Patent number: 4650873Abstract: Processes for the preparation of the antiarrhythmic agent 2,5-bis(2,2,2-trifluoroethoxy)-N-(2-piperidylmethyl)-benzamide.Type: GrantFiled: May 1, 1986Date of Patent: March 17, 1987Assignee: Riker LaboratoriesInventor: Charles M. Leir
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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: 4578520Abstract: Novel compounds of general formula I ##STR1## wherein R is a branched or unbranched alkyl, cycloalkyl, or aralkyl group, which group optionally contains or is substituted by a halogen or oxygen function, the oxygen function optionally being in the form of an alcohol or ether moiety;R.sub.1, R.sub.2, and R.sub.3, which may be the same or different, is hydrogen, an alkyl, acyl, or benzoyl group, which group optionally contains or is substituted by a halogen or oxygen function;R.sub.4 is hydrogen, an alkyl, alkenyl preferably being an allyl or prenyl group, or aralkyl group which group optionally contains or is substituted by an alkyl, aryl, halogen or oxygen function;R.sub.5 is hydrogen, an alkyl, aralkyl, acyl, or aryl group, which group optionally contains or is substituted by an alkyl, aryl, halogen, or oxygen function; except that R.sub.4 and R.sub.5 are not both hydrogen;and except for the compounds when R.sub.Type: GrantFiled: December 7, 1984Date of Patent: March 25, 1986Assignee: Noristan LimitedInventors: Theunis G. Fourie, Theodor G. Dekker, Friedrich O. Snyckers, Cornelis J. van der Schyf
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Patent number: 4546184Abstract: The invention relates to a novel fluorinated pre-polymer and novel process steps in producing the same. The pre-polymers are quinoxaline materials derived by reaction of diketone linkage containing perfluoro-compounds with an aromatic diamine. The diketone is produced by oxidatively dechlorinating a polychloroketone which may be a monoketone or a bis-ketone. The polychloroketone is produced by reacting a keto-ylid with a chlorinating agent, e.g., chlorine. The keto-ylid is produced by reacting a phosphorane with an acid halide of a polyoxy-perfluoroalkylene oxide wherein the perfluoro-oxyalkylene group contains two or three carbon atoms, and there are present from two to twenty perfluoro-oxyalkylene units in the oligomer. The quinoxalines, the polychloroketones and the diketones hereof are novel products. Cross-linking may be effected with a free radical generator.Type: GrantFiled: May 23, 1983Date of Patent: October 8, 1985Assignee: SCM CorporationInventor: Keith B. Baucom
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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: 4533754Abstract: A process for the preparation of aldehydes of the formula ##STR1## wherein R is a substituted or unsubstituted aryl group containing one or more benzenoid rings which comprises reacting an aryl acid halide with an organozinc compound in solvent in the presence of a palladium metal complex catalyst.Type: GrantFiled: July 23, 1984Date of Patent: August 6, 1985Assignee: Atlantic Richfield CompanyInventor: Roger A. Grey
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Patent number: 4529490Abstract: Aryliodonium salts resulting from the condensation of aryliodosotosylates and aryl ketones are provided which are used as photoinitiators to effect deep section UV cures. Deep section photopolymerizable organic materials are also provided which can be used as encapsulating agents to encapsulate a wide variety of electronic components.Type: GrantFiled: May 23, 1983Date of Patent: July 16, 1985Assignee: General Electric CompanyInventors: James V. Crivello, Julia L. Lee
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Patent number: 4492800Abstract: A process for the preparation of a 1,1-dichloro-alkene of the formula ##STR1## in which R.sup.1 is hydrogen, or an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, andR.sup.2 is an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, orR.sup.1 and R.sup.2 together form an optionally branched and/or optionally benzo-fused hydrocarbon chain,comprising reacting a carbonyl compound of the formula ##STR2## with a trichloromethanephosphonic acid ester of the formula ##STR3## in which R.sup.3 each individually is an alkyl or phenyl radical, or together are alkanediyl,in the presence of at least an equimolar amount of magnesium. Advantageously,R.sup.1 is hydrogen,R.sup.2 is a C.sub.2 to C.sub.5 alkenyl radical or a radical of the formula ##STR4## Z is a cyano, acetal, carboxyl or C.sub.1 to C.sub.4 alkoxycarbonyl radical, or a radical of the formula COOM, andM is sodium or potassium,R.sup.3 each individually is a C.sub.1 to C.Type: GrantFiled: February 22, 1983Date of Patent: January 8, 1985Assignee: Bayer AktiengesellschaftInventors: Fritz Maurer, Uwe Priesnitz, Hans-Jochem Riebel
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Patent number: 4487969Abstract: A process for the production of m-fluoroacetophenone comprises reacting m-aminoacetophenone with a diazotization agent in the presence of hydrogen fluoride. The diazonium fluoride compound produced is decomposed by heating to produce highly pure m-fluoroacetophenone in good yields.Type: GrantFiled: September 30, 1982Date of Patent: December 11, 1984Assignee: Olin CorporationInventor: Max M. Boudakian
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Patent number: 4474932Abstract: Aromatic ethers or polyethers are produced by reacting aromatic fluorine compounds, in which one or more fluorine substituents are attached to an aromatic nucleus, with trialkyl silyl derivatives of phenols, in which one or more trialkyl silyl groups are attached to the residue of a mono- or polyphenol, or by reacting trialkyl silyl derivatives of fluorophenols with elimination of trialkylfluorosilane.Type: GrantFiled: March 16, 1983Date of Patent: October 2, 1984Assignee: Bayer AktiengesellschaftInventors: Gerhard Bier, Hans R. Kricheldorf
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Patent number: 4453009Abstract: 4-Fluorobenzophenone derivatives of 4,4'-difluorobenzophenone are produced by effecting a halogen-fluorine exchanging reaction between the corresponding 4-halogenobenzophenone derivatives or 4,4'-dihalogenobenzophenone and an alkali fluoride.The reaction is carried out by heating in an organic solvent. After distilling off the solvent from the reaction product mixture, the end product is isolated by extracting with a solvent. Alternatively the end product is isolated by distillation.Type: GrantFiled: October 8, 1982Date of Patent: June 5, 1984Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Akihiro Yamaguchi, Keizaburo Yamaguchi, Kenichi Sugimoto, Yoshimitsu Tanabe
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Patent number: 4450296Abstract: A process for producing 2-methyl-2-phenyl-4-hexanone comprising reacting the Grignard reagent having the structure: ##STR1## with propianic anhydride having the structure: ##STR2##Type: GrantFiled: February 5, 1981Date of Patent: May 22, 1984Assignee: International Flavors & Fragrances Inc.Inventor: Takao Yoshida
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Patent number: 4440694Abstract: The invention relates to vinylstilbene compounds of the formula ##STR1## wherein Q is the grouping --COX or ##STR2## These compounds are obtained by reacting 1 molar equivalent of a compound of the formula II ##STR3## wherein X is chlorine, bromine or iodine, in the presence of a base and with the addition of palladium metal or of palladium compounds, as catalyst, which, under the reaction conditions, form labile palladium(O) compounds which do not contain phosphorus, with 1 molar equivalent of a compound of the formula III or with 1 molar equivalent of each of the compounds of the formulae III and IV ##STR4##Type: GrantFiled: May 8, 1981Date of Patent: April 3, 1984Assignee: Ciba-Geigy CorporationInventors: Daniel Bellus, Hans-Ulrich Blaser, Guglielmo Kabas, Dieter Reinehr, Alwyn Spencer, Kurt Weber
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Patent number: 4422870Abstract: 2-Aryl-1, 3-cyclohexanedione enol ester compounds exhibit outstanding miticidal,mite ovicidal and herbicidal activity.Type: GrantFiled: March 28, 1977Date of Patent: December 27, 1983Assignee: Union Carbide CorporationInventor: Thomas N. Wheeler