Oxy Containing Reactant Patents (Class 568/315)
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Patent number: 6395939Abstract: One aspect of the present invention relates to novel reaction conditions that allow the efficient synthesis of diaryl ethers from arenes bearing a leaving group and arenols under relatively mild conditions. Another aspect of the present invention relates to the dramatic effects of acidic activators on Ullmann-type couplings involving electron-poor and/or relatively insoluble substrates.Type: GrantFiled: October 5, 1998Date of Patent: May 28, 2002Assignee: Massachusetts Institute of TechnologyInventors: Jean-Francois Marcoux, Sven Doye, Stephen Buchwald
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Patent number: 6303823Abstract: A process for preparing ketones by so-called “crossed aldol condensation” of a ketone with an aldehyde in the presence of a catalyst system consisting of approximately equimolar amounts of a secondary amine and of a carboxylic acid containing at least 2 C atoms, to form an &agr;,&bgr;-unsaturated ketone, and, where appropriate, subsequent catalytic hydrogenation. The process is used in particular for preparing 6-methyl-3-hepten-2-one by reacting acetone with isovaleraldehyde, and for preparing its hydrogenation product, 6-methylheptan-2-one, which is an important precursor for numerous active substances, in particular for preparing lipid-soluble vitamins such as vitamin E.Type: GrantFiled: December 5, 2000Date of Patent: October 16, 2001Assignee: BASF AktiengesellschaftInventors: Andreas Kramer, Christian Knoll, Johann-Peter Melder, Wolfgang Siegel, Gerd Kaibel
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Patent number: 6245944Abstract: A process for preparing a compound of the formula I where R1 and R2 are hydrogen or C1-C4-alkyl and R3 is C1-C10-alkyl, phenyl or C1-C4-alkyl-substituted phenyl, comprises reacting a compound II with a compound of the formula III where X is chlorine, bromine or iodine, in the presence of a Friedel-Crafts catalyst in one step to give a compound I.Type: GrantFiled: December 9, 1998Date of Patent: June 12, 2001Assignee: BASF AktiengesellschaftInventors: Carsten Süling, Heike Gregorius, Walter Dobler, Roland Hingmann, Bernhard Rieger, Ulf Dietrich, Jürgen Matthäus Wagner, Hans-Joachim Müller
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Patent number: 6242641Abstract: The present invention relates to compounds selected from formula I wherein R1, R2, R3 and R4 are the same or different and represent hydrogen, C1, to C6-alkyl, C5 to C6-cycloalkyl, phenyl and halogen, m and n are the same or different and represent the 2, 3, 4 or 5, X, A and B represent carbon and Y1, Y2, Z1 and Z2 are the same or different and represent hydrogen, hydroxyl (OH), amino (NH2), isocyanato (NCO) or 4-hydroxyphenyl.Type: GrantFiled: March 22, 1999Date of Patent: June 5, 2001Assignee: Bayer AktiengesellschaftInventors: Manfred Jautelat, Carl Casser, Hanns-Peter Müller, Manfred Hajek
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Patent number: 6159988Abstract: Compounds of formula I, ##STR1## and the physiologically tolerable salts thereof, wherein the substituents R.sub.1 -R.sub.4 have the meanings given in the specifications and show an activity against inflammatory conditions.Type: GrantFiled: June 29, 1998Date of Patent: December 12, 2000Assignee: Hoeschst AktiengesellschaftInventors: Ramachandra Ganapati Naik, Vilas Narayan Mumbaikar, Ravishankar Vasumathy, Aftab Dawoodbhai Lakdawala, Mandakini Bipin Alreja, Bansi Lal, Jurgen Blumbach, Klaus Ulrich Weithmann, Robert Ryder Bartlett, Kalpana Sanjay Joshi, Swati Bal-Tembe, Sadagopan Raghavan
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Preparation of 5-(3-butyryl-2,4,6-trimethyl)-2-(1-(ethoxyimino)propyl)-3-hydroxycyclohe x-2-en-1-one
Patent number: 6147260Abstract: A process of preparing the compound of formula (I) which comprises: (a) reacting butyryl chloride with the compound of formula (IV) in the presence of a Friedel-Crafts catalyst in an inert diluent to produce a compound of formula (II) and (b) reacting the compound of formula (II) with ethoxyamine. Compound (II) is also claimed.Type: GrantFiled: June 21, 1999Date of Patent: November 14, 2000Assignee: Orica Australia PTY, LTDInventors: Graham John Bird, Keith Geoffrey Watson -
Patent number: 6143935Abstract: The condensation reaction of a ketone with either an ester or a carbonate to form, respectively, a 1,3-diketone or a .beta.-ketoester often affords poor results under the standard condensation reaction conditions. High yields and high purities of the desired product can be obtained by performing the reaction using an alkoxide base in DMSO as the sole solvent.Type: GrantFiled: June 2, 1998Date of Patent: November 7, 2000Assignee: Eastman Chemical CompanyInventors: Neil W. Boaz, M. Todd Coleman
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Patent number: 6034279Abstract: An improved process is described for preparing .gamma.,.delta.-unsaturated ke-tones, which are in demand as aroma substances and intermediates for vitamins and carotenoids, by reacting tertiary allyl alcohols and alkenyl alkyl ethers in the presence of acid catalysts at elevated temperature, which comprises carrying out the reaction in the presence of a phosphorus derivative of the formula IV ##STR1## where A and B are each a branched or unbranched alkyl or alkoxy having from 1 to 10 carbons, a substituted or unsubstituted aryl, cycloalkyl, aryloxy or cycloaryloxy;A can additionally be --H or --OH orA and B together are a substituted or unsubstituted tetramethylene or pentamethylene or substituted or unsubstituted phenyl-1,2-diol or 1,1'-binaphthyl-2,2'-diol.Type: GrantFiled: January 29, 1999Date of Patent: March 7, 2000Assignee: BASF AktiengesellschaftInventors: Stefan Kashammer, Detlef Ruff
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Patent number: 5969185Abstract: A process for making a phenolic ketone involving reacting a metal aryloxide with an aliphatic aldehyde having from at least 2 to about 25 carbon atoms.Type: GrantFiled: June 24, 1998Date of Patent: October 19, 1999Assignee: Henkel CorporationInventor: Sang I. Kang
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Patent number: 5936129Abstract: A process for making a sterically-hindered beta-diketone involving: (a) providing a solution comprising: (i) an ester; (ii) a base; and (iii) a solvent; (b) adding a ketone selected from the group consisting of an aromatic ketone and a hindered aliphatic ketone, to the solution, to form a condensation reaction mixture, whereby either the ester or the ketone is hindered; (c) reacting the solution with the ketone to form a sterically-hindered beta-diketone; and (d) recovering the sterically-hindered beta-diketone from the condensation reaction mixture.Type: GrantFiled: January 22, 1998Date of Patent: August 10, 1999Assignee: Henkel CorporationInventors: Kevin V. Martin, Phillip L. Mattison, Michael J. Virnig
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Patent number: 5849955Abstract: A process is described for the synthesis of 2-hydroxy-4-alkyloxy benzophenone by the selective alkylation of 2,4-dihydroxy benzophenone with a dialkyl carbonate, in liquid phase, in the presence of suitable catalysts, at a temperature ranging between 120.degree. and 220.degree. C. and at a total pressure ranging from 2 to 60 ate.Type: GrantFiled: November 20, 1997Date of Patent: December 15, 1998Assignee: Enichem S.p.A.Inventors: Marcello Notari, Franco Mizia, Franco Rivetti
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Patent number: 5786514Abstract: A process for alkoxylating phenols is disclosed. The process comprises reacting a carbonyl-functionalized phenol with an alkylene oxide in the presence of a substantially non-crystalline double metal cyanide (DMC) catalyst. The process offers fast reaction times at low catalyst levels, reduced problems with condensation side reactions, and low-color, low-viscosity, low-polydispersity alkoxylated phenols. The process enables efficient preparation of alkoxylated carbonyl-functonalized phenols that are especially valuable in the surfactant industry.Type: GrantFiled: December 18, 1996Date of Patent: July 28, 1998Assignee: Arco Chemical Technology, L.P.Inventors: Jianzhong Shen, Sujuan Ba, David M. Braunstein, Haven S. Kesling, Jr.
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Patent number: 5750793Abstract: New process for the synthesis of the antiinflammatory drug known as nabumetone that consists in reacting 2-acetyl-5-bromo-6-methoxynaphthalene with an alkyl acetate in presence of an alkaline alcoholate to get 4-(5-bromo-6-methoxy-2-naphthyl)-4-hydroxybut-3-en-2-one that by catalytic hydrogenation in a polar solvent and in presence of a base gives 4-(6-methoxy-2-naphthyl)butan-2-one known as nabumetone.Type: GrantFiled: January 23, 1997Date of Patent: May 12, 1998Assignee: Alfa Chemicals Italiana S.p.A.Inventors: Vincenzo Cannata, Amilcare Bertoni, Stefano Bianchi
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Patent number: 5728888Abstract: Hydroxylated benzophenonens are prepared from completely or partially methylated hydroxybenzophenones by reacting these methyl ethers with AlCl.sub.3 and subsequently hydrolyzing with water, the reaction being carried out in the presence of one or more compounds from the class of ureas or carboxamides.Type: GrantFiled: February 21, 1997Date of Patent: March 17, 1998Assignee: BASF AktiengesellschaftInventors: Alexander Aumuller, Gunter Brill, Peter Bottcher
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Patent number: 5670651Abstract: Benzocyclobutene-terminated monomers of the formula ##STR1## wherein Ar is --SO.sub.2 --, --CO--, or ##STR2## are prepared by reacting a benzocyclobutene of the formula ##STR3## wherein R is --H or --SiMe.sub.3, with a difluorophenyl compound of the formula ##STR4## wherein Ar is as described previously, in the presence of a promoter. A mixture of the resins is obtained when potassium carbonate is employed as the promoter. The bis(benzocyclobutene)-terminated monomer is obtained when cesium fluoride is employed as the promoter.Type: GrantFiled: February 12, 1996Date of Patent: September 23, 1997Assignee: The United States of America as represented by the Secretary of the Air ForceInventors: Loon-Seng Tan, Narayanan Venkatasubramanian
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Patent number: 5663447Abstract: A particularly advantageous process for the preparation of 2,2-dialkyl-arylidene-cycloalkanones is characterized in that 2-alkyl-arylidene-cycloalkanones are reacted with alkyl halides in the presence of metal hydroxides and tertiary alcohols.Type: GrantFiled: June 20, 1996Date of Patent: September 2, 1997Assignee: Bayer AktiengesellschaftInventors: Nikolaus Muller, Thomas Essert
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Patent number: 5618982Abstract: Ketones having at least one hydrogen atom or ester group in the .alpha.-position with respect to a ketonic carbonyl group thereof, for example cyclopentanone, 2-methylcyclopentanone and other substituted cyclopentanones, are effectively C- or .alpha.-alkylated, especially on an industrial scale, by reacting same with an alkylating agent in the presence of a catalytically effective amount of a condensed or uncondensed orthophosphate anion.Type: GrantFiled: November 22, 1994Date of Patent: April 8, 1997Assignee: Rhone-Poulenc ChimieInventors: Laurent Gilbert, Michel Spagnol
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Patent number: 5600008Abstract: The present invention relates to novel 4-halo-2-fluoro-5-alkoxybenzoyl compounds and their methods of manufacture. These compounds are useful for the preparation of agricultural chemicals and medicines, particularly as intermediates for an active class of arylhaloalkylpyrazole and aryl alkylsulfonylpyrazole herbicides.Type: GrantFiled: March 13, 1995Date of Patent: February 4, 1997Assignee: Monsanto CompanyInventors: Bruce C. Hamper, Kindrick L. Leschinsky
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Patent number: 5600009Abstract: The palladium-catalyzed coupling of aryl and vinyl halides with vinylic compounds is disclosed. A preferred embodiment relating to the palladium catalyzed coupling of 4-substituted and 6-substituted-2-methoxynaphthalene to form nabumetone is also disclosed. The beauty of this novel reaction is that methylvinylketone, normally employed by the art directly as-is for the preparation of nabumetone, is formed in situ. We have discovered a mechanism to take advantage of the in situ formation of methylvinylketone, thus avoiding the use of expensive, toxic, and unstable methyl vinyl ketone feed. This reaction may be employed for a variety of pharmaceutically active and non-pharmaceutical compounds.Type: GrantFiled: April 9, 1996Date of Patent: February 4, 1997Assignee: Hoechst Celanese CorporationInventors: John F. Fritch, Mohammad Aslam, Dora E. Rios, Joel C. Smith
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Patent number: 5527769Abstract: The compounds of formula ##STR1## wherein symbol X represents a --CHO group or an acetal group of formula ##STR2## symbols R', taken separately, represent each a C.sub.1 to C.sub.4, linear or branched, saturated or unsaturated, hydrocarbon radical or, taken together, represent a C.sub.1 to C.sub.4 alkylene radical, which may be substituted, and symbol R represents a hydrogen atom or a methyl radical, are useful as perfuming ingredients for the preparation of perfuming compositions and perfumed articles, to which they impart floral type notes.Type: GrantFiled: January 13, 1995Date of Patent: June 18, 1996Assignee: Firmenich SAInventors: Beat Winter, George Skouroumounis
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Patent number: 5504255Abstract: The present invention provides special epoxy derivative (1), cyclohexanone derivative (2), cyclohexenone derivative (3) and 3-substituted cyclohexenone derivative (4) which are useful as intermediates for synthesizing physiologically active materials, and a method for stereoselectively introducing substituted groups. Further, the present invention provides a method for synthesizing optically active compounds, such as optically active carvone via these intermediates.Type: GrantFiled: May 15, 1995Date of Patent: April 2, 1996Assignee: Chisso CorporationInventors: Seiichi Takano, Kunio Ogasawara
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Patent number: 5466873Abstract: Arylketoamines are prepared by reacting arylisonitrosoalkanones with hydrogen in the presence of a transition metal catalyst and a liquid carboxylic acid at a temperature of less than about 600.degree. C.Type: GrantFiled: November 30, 1994Date of Patent: November 14, 1995Assignee: Hoechst Celanese CorporationInventors: Ahmed M. Tafesh, George Kvakovszky, Charlet R. Lindley
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Patent number: 5446175Abstract: The present invention provides special epoxy derivative (1), cyclohexanone derivative (2), cyclohexenone derivative (3) and 3-substituted cyclohexenone derivative (4) which are useful as intermediates for synthesizing physiologically active materials, and a method for stereoselectively introducing substituted groups. Further, the present invention provides a method for synthesizing optically active compounds, such as optically active carvone via these intermediates.Type: GrantFiled: July 19, 1994Date of Patent: August 29, 1995Assignee: Chisso CorporationInventors: Seiichi Takano, Kunio Ogasawara
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Patent number: 5434289Abstract: A process for producing an optically active .beta.-hydroxyketone represented by formula (I): ##STR1## by catalytic asymmetrical aldol reaction is disclosed, comprising reacting a silyl-enol ether represented by formula (II): ##STR2## with a substituted aldehyde represented by formula (III):R.sup.5 CHO (III)in the presence of a binaphthol-titanium complex represented by formula (IV): ##STR3## An optically active .beta.-hydroxyketone is efficiently produced with diastereo-specificity and enantio-specificity.Type: GrantFiled: March 10, 1994Date of Patent: July 18, 1995Assignee: Takasago International CorporationInventors: Koichi Mikami, Satoru Matsukawa, Masaki Shimizu, Masahiro Terada, Noboru Sayo
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Patent number: 5430172Abstract: A process for preparing 4-alkanoylaryl benzyl ethers of the general formula I ##STR1## where R is hydrogen, halogen, cyano; alkyl, alkoxy;X is CH.sub.2, CH--CH.sub.3, CH--CH.sub.2 --CH.sub.3, CH--OCH.sub.3 or N--OCH.sub.3 ;Y is oxygen, sulfur, direct linkage or nitrogen;m is 0, 1, 2 or 3;R.sup.1 is hydrogen; alkyl, alkenyl, alkynyl or alkoxy;R.sup.2 is cyano, halogen, alkyl, alkoxy or haloalkyl;R.sup.3 is alkyl; haloalkyl; cycloalkyl; or an unsubstituted or substituted mono- to trinuclear aromatic system,comprises reacting an aryl benzyl ether of the general formula II ##STR2## where X, Y, R, R.sup.1, R.sup.2 and m have the abovementioned meanings, with a carbonyl halide or with a carboxylic anhydride or with a carboxylic sulfonic anhydride in the presence of an acid and in the presence or absence of a diluent.Type: GrantFiled: April 15, 1994Date of Patent: July 4, 1995Assignee: BASF AktiengesellschaftInventors: Wassilios Grammenos, Wolfgang Siegel, Klaus Oberdorf, Bernd Mueller, Hubert Sauter, Reinhard Doetzer
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Patent number: 5426233Abstract: A process for preparing an hydroxyketone of the formula (X): ##STR1## wherein Ar represents substituted phenyl, aromatic heterocyclic, or substituted aromatic heterocyclic; R.sup.1 and R.sup.2 independently represents hydrogen, C-1 to C-16 alkyl, aromatic, substituted aromatic, aromatic heterocyclic, substituted aromatic heterocyclic or C-1 to C-5 alkyl covalently bonded to Ar, with the provision that R.sup.1 and R.sup.2 are different. The process comprises contacting a compound of the formula (V): ##STR2## with a solvent, a base and a chiral hydroxylating agent at a temperature of about -85.degree. C. or less.Compounds of the formulae ##STR3## also are disclosed.Type: GrantFiled: September 23, 1993Date of Patent: June 20, 1995Assignee: Schering CorporationInventor: Dinesh Gala
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Patent number: 5395953Abstract: The invention relates to a method of preparing a compound having an alkyl or alkoxyalkyl side-chain with a terminal 2-hydroxyprop-2-yl group, by oxidizing a compound having a terminal isopropyl group in its side-chain with a dioxirane as the oxidant.Type: GrantFiled: August 20, 1993Date of Patent: March 7, 1995Assignee: Duphar International Research B.V.Inventors: Miguel A. Maestro, Antonio Mourino, Benjamin Borsje, Sebastianus J. Halkes
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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: 5347049Abstract: Di-amines endowed with chain extension activity for formulations such as polyureas and polyurethanes are disclosed, and which have the general formula: ##STR1## wherein n is 0-1000; R.sub.1, R.sub.2, R.sub.5, and R.sub.6 are each independently selected from the group consisting of H, --CH.sub.3, --CH.sub.2 CH.sub.3, --CH.sub.2 OH, and --CH.sub.2 --CH.sub.2 --OH; R.sub.3 =R.sub.4, and R.sub.3 and R.sub.4 are from the group --CH.sub.2 CH.sub.2 --; --CH.sub.2 --C(CH.sub.3)H--; and --C(CH.sub.3) H--CH.sub.2 --; and the diasteromeric salts thereof.Type: GrantFiled: January 11, 1994Date of Patent: September 13, 1994Assignee: Hoechst Celanese CorporationInventors: Michael T. Sheehan, James R. Sounik, Bret F. Hann, William W. Wilkison, III
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Patent number: 5347051Abstract: Amines endowed with chain extension activity for formulations such as polyureas and polyurethanes are disclosed, which have the general formula: ##STR1## wherein n is 0-1000; R.sub.1 .dbd.R.sub.2, and R.sub.1 and R.sub.2 are from the group --CH.sub.2 --CH.sub.2 --; --CH.sub.2 --C(CH.sub.3)H--; and --C(CH.sub.3)H--CH.sub.2 --; and R.sub.3 and R.sub.4 are each independently selected from the group consisting of H, --CH.sub.3, --CH.sub.2 CH.sub.3, --CH.sub.2 OH, and --CH.sub.2 --CH.sub.2 --OH; and the diasteromeric salts thereof.Type: GrantFiled: January 11, 1994Date of Patent: September 13, 1994Assignee: Hoechst Celanese CorporationInventors: Michael T. Sheehan, James R. Sounik, Bret F. Hann, William W. Wilkison, III
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Patent number: 5266344Abstract: The present invention relates to a novel compound tetrahydrocurcumin and a substance containing the same, which are produced from curcumin or a substance containing it as a material. This substance has characteristic properties such as strong antioxidative activity and yellowish color generated from reducing the original color of curcumin. The curcumin is being produced from a Zingiberaceae plant classified into Curcuma longa as a tropical product and is used for a spice and a yellow pigment for curry powder and pickles. The present invention further relates to the production method.Type: GrantFiled: November 20, 1990Date of Patent: November 30, 1993Assignee: Kabushiki Kaisha Kobe Seiko ShoInventors: Akio Mimura, Yoshimasa Takahara, Toshihiko Osawa
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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: 5225603Abstract: An intermediate for the manufacture of nabumetone, 4-(6'-methoxy-2'-naphthyl)-3-buten-2-one, is prepared by contacting 2-bromo-6-methoxynaphphalene with methyl vinyl ketone in the presence of a palladium catalyst at from about 50.degree. C. to about 200.degree. C. for a time sufficient to cause substantially complete reaction to occur.Type: GrantFiled: June 17, 1988Date of Patent: July 6, 1993Assignee: Hoechst Celanese CorporationInventors: Mohammad Aslam, Varadaraj Elango
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Patent number: 5210312Abstract: Process for the preparation of herbicidally active substituted cyclohexan-1,3,5-triones which comprises either(a) reacting a compound of formula (II) ##STR1## wherein R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are, for example, hydrogen or C.sub.1 -C.sub.4 alkyl with a compound of formula (III):R.sup.1 COCN (III)wherein R.sup.1 is optionally substituted aryl in the presence of a base and a Lewis acid; or(b) reacting a compound of formula (VI) ##STR2## with a compound of formula (X) ##STR3## in the presence of a Lewis acid; or (c) where R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are the same, reacting a compound of formula (XI) ##STR4## with a compound of formula R.sup.3 X' in the presence of a base, wherein X' is a leaving group.Type: GrantFiled: June 4, 1991Date of Patent: May 11, 1993Assignee: Imperial Chemical Industries PLCInventor: Glynn Mitchell
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Patent number: 5202495Abstract: A process for the preparation of the compound of formula (I), 3-(6'methoxy-2'-naphthylmethyl)-2,4-pentanedione, ##STR1## comprises the calalytic hydrogenation of a compound of formula (II): ##STR2##Type: GrantFiled: October 10, 1990Date of Patent: April 13, 1993Inventor: Sidney E. Callander
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Patent number: 5159117Abstract: A process for preparing .alpha.,.alpha.-dialkoxy ketones of the formula I ##STR1## where R.sup.1 and R.sup.2 are each, independently of one another, hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.3 -C.sub.20 -cycloalkyl, C.sub.4 -C.sub.30 -cycloalkylakyl, C.sub.9 -C.sub.30 -alkylcycloalkyl, unsubstituted or C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy-, halogen-, C.sub.1 -C.sub.4 -haloalkyl-, C.sub.1 -C.sub.4 -haloalkoxy-, phenyl-, phenoxy-, halophenyl-, halophenoxy- and/or cyano-substituted aryl, C.sub.7 -C.sub.20 -aralkyl or heterocyclyl,R.sup.2 is also ##STR2## R.sup.3 and R.sup.4 are each, independently of one another, C.sub.1 -C.sub.20 -alkyl, C.sub.3 -C.sub.20 -cycloalkyl, aryl, C.sub.7 -C.sub.20 -arylalkyl, or together are an unsubstituted or C.sub.1-C.sub.4 -alkyl- substituted C.sub.2 -C.sub.7 -alkylene chain andR.sup.5 is R.sup.1 or together with R.sup.1 is an unsubstituted or C.sub.1 -C.sub.4 -alkyl-substituted C.sub.2 -C.sub.Type: GrantFiled: August 20, 1991Date of Patent: October 27, 1992Assignee: BASF AktiengesellschaftInventors: Guenter Wegner, Stefan Karbach, Hubert Smuda, Eckhard Hickmann, Reiner Kober, Rainer Seele, Thomas Zierke
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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: 5120855Abstract: The present invention provides a method for producing a hydroxyaromatic ketoacetal from a hydroxyaromatic methylketone. The invention further provides a method for producing a hydroxyaromatic ketoaldehyde from a hydroxyaromatic ketoacetal. The hydroxyaromatic ketoaldehyde can be further reacted to form a hydantoin, which hydantoin can be hydrolyzed to produce a hydroxyphenylglycine.Type: GrantFiled: December 13, 1990Date of Patent: June 9, 1992Assignee: Hoechst Celanese CorporationInventors: Olan S. Fruchey, Graham N. Mott, John R. Durrwachter
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Patent number: 5118859Abstract: 2-Hydroxy-4-(2'-hydroxyethoxy)phenyl aryl ketones I ##STR1## where Ar is substituted or unsubstituted aryl, are prepared by reacting 2,4-dihydroxyphenyl aryl ketones II ##STR2## with ethylene carbonate in the presence of an alkali metal or alkaline earth metal salt of a carboxylic acid as catalyst and purified with sodium dithionite.Type: GrantFiled: October 22, 1990Date of Patent: June 2, 1992Assignee: BASF AktiengesellschaftInventors: Alexander Aumueller, Wolfgang Goetze
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Patent number: 5082975Abstract: A process for making hexahydrolupulone is described which involves the separation of beta acids from a hop extract, the removal of catalyst poisons from the beta acids, the hydrogenation of the beta acids to hexahydrolupulone, and the purification of the resulting hexahydrolupulone. Its use as an inhibitor of the growth of unwanted types of cells is described, as well as preferred forms for such use.Type: GrantFiled: February 26, 1990Date of Patent: January 21, 1992Assignee: Kalamazoo Holdings, Inc.Inventors: Paul H. Todd, Jr., James A. Guzinski
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Patent number: 5081307Abstract: 2,2-Dimethoxy-2-phenylacetophenone is prepared by reacting benzil with dimethyl sulfate and alkali metal methylate in a nonpolar organic solvent (e.g. xylene, cyclohexane) in the presence of one or more of catalysts selected from the group consisting of polyethylene glycol, a polyethylene glycol dialkyl ether and a crown ether. The reaction can be carried out more preferably in the presence of diglyme or triglyme or a mixture of diglyme or triglyme and polyethylene glycol.Type: GrantFiled: July 5, 1990Date of Patent: January 14, 1992Assignee: Kawaguchi Chemical Co., Ltd.Inventors: Soichi Kitamura, Masaru Tomioka, Hidekuni Gotoh
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Patent number: 5068447Abstract: 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 an inorganic salt controlling agent, for example, lithium chloride, 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: July 6, 1990Date of Patent: November 26, 1991Assignee: Raychem CorporationInventors: Heinrich C. Gors, Patrick J. Horner, Viktors Jansons
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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: 4980513Abstract: A process for making a hydrocarbyl vinyl ketone is disclosed. In this process a ketone having the structural formula CH.sub.3 COR, where R is lower alkyl, phenyl or C.sub.7 -C.sub.8 aralkyl, is reacted with methanol in an oxygen-containing atmosphere in the presence of a catalyst system comprising a catalytically effective amount of iron on an inert support. In another preferred embodiment, the catalyst system comprises a catalytically effective amount of a precious metal selected from the group consisting of silver and gold, in addition to iron, supported on an inert material.Type: GrantFiled: January 4, 1990Date of Patent: December 25, 1990Assignee: Quantum Chemical CorporationInventors: Thomas S. Brima, Ronnie M. Hanes
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Patent number: 4980512Abstract: Alkoxybenzophenones of the formula (I) ##STR1## wherein R.sup.1 is C.sub.1 -C.sub.4 -alkyl and R.sup.2 and R.sup.3 independently of one another are each hydrogen, hydroxy, C.sub.1 -C.sub.8 -alkoxy, C.sub.1 -C.sub.4 -alkyl or halogen, are prepared by reacting a benzophenone of the formula (II) ##STR2## with a dialkyl sulfate of the formula (III)(R.sup.1 O).sub.2 SO.sub.2 (III)where, in the formulae, R.sup.1, R.sup.2 and R.sup.3 have the above-mentioned meanings, by a process in which the reaction is carried out in water as the reaction medium in the presence of a base, and the dialkyl sulfate (III) is added a little at a time.The process gives (I) in high yield and virtually free of 2,4-dialkoxybenzophenones.Type: GrantFiled: October 13, 1989Date of Patent: December 25, 1990Assignee: BASF AktiengesellschaftInventors: Alexander Aumueller, Peter Neumann
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Patent number: 4978797Abstract: The present invention relates to an improved process for the preparation of 2-hydroxy-4-(hydroxyalkoxy)-benzophenone. More particularly the invention is directed to the oxyalkylation of 2,4-dihydroxy benzophenone, using C.sub.2 to C.sub.4 alkylene oxides in the presence of a basic catalyst and water. Such products are useful as ultraviolet light absorbers.Type: GrantFiled: November 21, 1989Date of Patent: December 18, 1990Assignee: BASF CorporationInventors: Bongsub Kim, Hermann Kaack
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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: 4970345Abstract: A process for preparing oxocyclopentenes of the formula: ##STR1## wherein R.sup.1 is hydrogen, lower alkyl or lower alkenyl and R.sup.2 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, substituted or unsubstituted aryl, ar(lower)alkyl, thienyl or cycloalkyl, which comprises subjecting a furan-carbinol of the formula: ##STR2## wherein R.sup.1 is as defined above and R.sup.3 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, substituted or unsubstituted aryl, ar(lower)alkyl, thienyl or cycloalkyl to rearrangement, subjecting the resultant hydroxycyclopentenone of the formula: ##STR3## wherein R.sup.1 and R.sup.3 are each as defined above to hydrogenation and subjecting the resulting hydroxycyclopentanone of the formula; ##STR4## wherein R.sup.1 and R.sup.2 are each as defined above to dehydration.Type: GrantFiled: February 20, 1986Date of Patent: November 13, 1990Assignee: Sumitomo Chemical Company, LimitedInventor: Masayoshi Minai
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Patent number: 4967010Abstract: Symmetric and asymmetric monoacetals of aromatic 1,2-diketones are prepared by a novel process, in a nonpolar solvent in the presence of a urea derivative as the catalyst.Type: GrantFiled: September 19, 1989Date of Patent: October 30, 1990Assignee: BASF AktiengesellschaftInventor: Andreas Boettcher
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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