Isomerization Patents (Class 568/310)
  • Patent number: 8283499
    Abstract: The present invention relates the use of 2,3-dihalonaphthoquinone compounds of Formula I wherein R1 and R2 are leaving groups like halogens selected from the group comprising Cl, Br, I and F and the R1 and R2 may be the same halogen or may contain different halogen groups, or sulphonyl groups, for making napthoquinone compounds of Formula IA wherein X is any aryl, heteroaryl, alkyl, cyclohexyl, substituted cylohexyl groups and the like.
    Type: Grant
    Filed: March 6, 2009
    Date of Patent: October 9, 2012
    Assignee: Alkem Laboratories Limited
    Inventors: Sanjay Sukumar Saralya, Shashikumar Hiriyalu Somashekar, Shashiprabha, Shridhara Kanakamajalu, Koottungalmadhom Ramaswamy Ranganathan, Veerasamy Ananthalakshmi, Govindarajalu Jeyaraman, Kothapalli Sundarraja Rao, Kuppuswamy Nagarajan
  • Publication number: 20110009574
    Abstract: A modified dimethylnaphthalene formaldehyde resin is disclosed, which is excellent in heat resistance and useful for thermosetting resins which are used for an electrical insulating material, a resin for resist, a semiconductor sealing resin, an adhesive for printed wiring board, a matrix resin for electrical laminate or prepreg to be mounted in electrical instruments, electronic instruments, industrial instruments, etc.
    Type: Application
    Filed: December 4, 2008
    Publication date: January 13, 2011
    Applicant: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Seiji Kita, Masashi Ogiwara, Mitsuharu Kitamura, Dai Oguro, Gou Higashihara
  • Patent number: 7847127
    Abstract: Disclosed herein is a novel process for preparation of atovaquone. The process includes reacting 1,4-naphthoquinone with trans-4-(4-chlorophenyl) cyclohexane carboxylic acid followed by halogenation to obtain a dihalo-compound. Further, dehydrohalogenation of the dihalo-compound produces a monohalogeno-compound which under goes hydrolysis to produce atovaquone. The invention also discloses atovaquone in a substantially pure and well defined polymorphic form designated as “Form IPCA-ATO,” and the preparation thereof.
    Type: Grant
    Filed: October 21, 2009
    Date of Patent: December 7, 2010
    Assignee: IPCA Laboratories Limited
    Inventors: Ashok Kumar, Suneel Yeshwant Dike, Pramil Kumar Mathur, Nellithanath Thankachen Byju, Brajesh Sharma, Swapnil Shreekant Kore, Vitthal Suryabhan Buchude, Dharmendra Singh
  • Patent number: 7816563
    Abstract: Improved methods of preparing hypocrellin B from 4,9-dihydroxy-3,10-perylenequinones are described.
    Type: Grant
    Filed: December 8, 2009
    Date of Patent: October 19, 2010
    Assignee: Alberta Innovates-Technology Futures
    Inventors: Minghui Du, Darol Maunder
  • Publication number: 20100081847
    Abstract: Disclosed herein is a novel process for preparation of atovaquone. The process includes reacting 1,4-naphthoquinone with trans-4-(4-chlorophenyl) cyclohexane carboxylic acid followed by halogenation to obtain a dihalo-compound. Further, dehydrohalogenation of the dihalo-compound produces a monohalogeno-compound which under goes hydrolysis to produce atovaquone. The invention also discloses atovaquone in a substantially pure and well defined polymorphic form designated as “Form IPCA-ATO,” and the preparation thereof.
    Type: Application
    Filed: October 21, 2009
    Publication date: April 1, 2010
    Inventors: Ashok Kumar, Suneel Yeshwant Dike, Pramilkumar Mathur, Nellithanath Thankachen Byju, Brajesh Sharma, Swapnil Shreekant Kore, Vitthal Suryabhan Buchude, Dharmendra Singh
  • Publication number: 20090311761
    Abstract: (3R)-3-Hydroxy-?-ionone and (3S)-3-hydroxy-?-ionone are two important intermediates in the synthesis of carotenoids with ?-end group such as lutein, zeaxanthin, ?-cryptoxanthin, and their stereoisomers. Among the various stereoisomers of these carotenoids, only (3R,3?R,6?R)-lutein, (3R,3?R)-zeaxanthin, and (3R)-?-cryptoxanthin are present in commonly consumed fruits and vegetables. There are 3 possible stereoisomers for zeaxanthin, these are: dietary (3R,3?R)-zeaxanthin (1), non-dietary (3S,3?S)-zeaxanthin (2), and non-dietary (3R,3?S;meso)-zeaxanthin (3) which is a presumed metabolite of dietary lutein. Dietary lutein as well as 1 and 3 are accumulated in the human macula and have been implicated in the prevention of age-related macular degeneration. (3R)-?-Cryptoxanthin (4) is also present in selected ocular tissues at a very low concentration whereas its enantiomer (3S)-?-cryptoxanthin (5) is absent in foods and human plasma.
    Type: Application
    Filed: June 15, 2009
    Publication date: December 17, 2009
    Inventors: Frederick Khachik, An-Ni Chang
  • Patent number: 7049455
    Abstract: In accordance with the invention, an industrial process for producing shogaols useful in the fields of for example foods, flavor, pharmaceutical products, qui-pharmaceutical products and cosmetics can be provided. The invention relates to novel intermediates represented by the following general formula and a process for producing shogaols from the intermediates. In accordance with the invention, shogaols can readily be produced, of which mass production has been difficult because shogaols have been produced only by the extraction process from a natural ginger. Intermediates; (in the formula (1), R1 represents hydrogen atom or methyl group; R2 represents optionally branched alkyl group with one to 18 carbon atoms; R3 and R4 each independently represents hydrogen atom, a lower alkyl group or a protective group of the phenolic hydroxyl group; A represents an alkylene group with one to 4 carbon atoms; and X represents benzenesulfonyl group or toluenesulfonyl group.
    Type: Grant
    Filed: April 25, 2003
    Date of Patent: May 23, 2006
    Assignee: Toagosei Co., Ltd.
    Inventors: Hisatoyo Kato, Shuhei Yamaguchi
  • Publication number: 20040152894
    Abstract: Processes for producing a compound represented by the formula (1), which includes an acrylic acid derivative and is useful as an agricultural chemical or medicine. One of the processes comprises the step of formulating a compound (3) and converting the OH of the resultant compound (2) into OR″. The first step comprises reacting a formic or orthoformic ester in the presence of a Lewis acid and a base. The second step comprises reacting the compound with R″OH or with R″OH and CH(OR″)3 under acidic conditions or using a phase-transfer catalyst in a two-phase system and regulating the base and the concentration thereof to stereoselectively synthesize the target compound. In another, process, the compound is efficiently produced without isolating the compound. The compound can also be produced without the compound (2).
    Type: Application
    Filed: January 14, 2004
    Publication date: August 5, 2004
    Applicant: Nippon Soda Co. Ltd
    Inventors: Yasuyuki Miyazawa, Takahiro Sagae, Yutaka Ishii, Hiroyuki Yazaki, Makoto Funabora, Mitsuru Takase, Yoshiyuki Iiyoshi, Satoru Yamazaki, Noriaki Kawahara
  • Patent number: 6331655
    Abstract: The present invention relates to a novel process for the preparation of aromatic carbonyl compounds by oxidative cleavage of styrenes using lipases and hydrogen peroxide or hydrogen peroxide donors in the presence of carboxylic acids or carboxylic esters.
    Type: Grant
    Filed: June 9, 2000
    Date of Patent: December 18, 2001
    Assignee: Haarmann & Reimer GmbH
    Inventors: Ian-Lucas Gatfield, Jens-Michael Hilmer
  • Patent number: 6310248
    Abstract: The invention relates to a process for the enantioselective preparation of tolterodine and analogues and salts thereof comprises the steps of: a) enantioselectively reducing the carbonyl function in a compound of formula (II): wherein R1, R2 and R3 independently of each other are hydrogen, methyl, methoxy, hydroxy, hydroxymethyl, carbamoyl, sulphamoyl or halogen, to form an enantiomerically enriched compound of formula (IIIa) or (IIIb): wherein R1, R2 and R3 are as defined above; b) subjecting the compound of formula (IIIa) or (IIIb) to a sigmatropic rearrangement to form a corresponding enantiomerically enriched compound of formula (IVa) or (IVb): wherein R1, R2 and R3 are as defined above; c) subjecting the compound of formula (IVa) or (IVb) to a Baeyer-Virliger oxidation to form a corresponding enantiomerically enriched compound of the general formula (Va) or (Vb): wherein R1, R2 and R3 are as defined above; d) converting the compo
    Type: Grant
    Filed: December 22, 2000
    Date of Patent: October 30, 2001
    Assignee: Pharmacia AB
    Inventors: Pher G. Andersson, Christian Hedberg
  • Patent number: 6251833
    Abstract: The present invention relates to novel 2-aryl-3-hydroxy-&Dgr;2-cyclopentene-1-one derivatives of the formula (I) in which A, B, D1, D2, G, W, X, Y and Z are each as defined in the description, to processes for their preparation and to their use as herbicides and pesticides.
    Type: Grant
    Filed: August 31, 1999
    Date of Patent: June 26, 2001
    Inventors: Christoph Erdelen, Ulrike Wachendorff-Neumann, Reiner Fischer, Alan Graff, Norbert Mencke, Andreas Turberg
  • Patent number: 6218579
    Abstract: A process for preparing a compound of Formula (I); where Q completes an optionally substituted 5-or 6-member saturated carbocyclic ring and R is optionally substituted phenyl or optionally substituted C3-C6 cycloalkyl which comprises the rearrangement of a compound of Formula (II); where Q and R are as defined in relation to Formula (I) in a polar aprotic, dipolar aprotic or aromatic hydrocarbon solvent in the presence of a moderate base and an azole.
    Type: Grant
    Filed: April 18, 2000
    Date of Patent: April 17, 2001
    Assignee: Zeneca Limited
    Inventors: Robert Oliver Jones, Thomas William Bentley, Stephen Martin Brown
  • Patent number: 5886231
    Abstract: A process for preparing a compound of formula (I): ##STR1## by rearrangement of a compound of formula (II): ##STR2## in a non-polar solvent in the presence of a cyanide source, an alkali or alkaline earth metal carbonate, a phase transfer catalyst and 1-6 moles of water with respect to the compound of formula (II).
    Type: Grant
    Filed: June 24, 1997
    Date of Patent: March 23, 1999
    Assignee: Zeneca Limited
    Inventors: Stephen Martin Brown, Howard Rawlinson
  • Patent number: 5840661
    Abstract: The present invention relates to novel 2-aryl-3-hydroxy-cyclopent-2-en-1-one derivatives of the formula (I) ##STR1## in which X represents halogen, nitro, cyano, alkyl, alkoxy, alkenyloxy, alkylthio, alkylsulphinyl, alkylsulphonyl, halogenoalkyl or halogenoalkoxy,Y represents hydrogen, halogen, nitro, cyano, alkyl, alkoxy, alkenyloxy, alkylthio, alkylsulphinyl, alkylsulphonyl, halogenoalkyl or halogenoalkoxy,Z represents halogen, nitro, cyano, alkyl, alkoxy or halogenoalkoxy andA, B, D.sup.1, D.sup.2, G and n have the meaning given in the description,several processes for their preparation and their use as compositions for controlling pests and as herbicides.
    Type: Grant
    Filed: December 31, 1996
    Date of Patent: November 24, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reiner Fischer, Jacques Dumas, Thomas Bretschneider, Christoph Erdelen, Ulrike Wachendorff-Neumann, Hans-Joachim Santel, Markus Dollinger, Andreas Turberg, Norbert Mencke
  • Patent number: 5457238
    Abstract: This invention concerns a process for the preparation of fluoroketones by the isomerization of corresponding epoxides, in the presence of an aluminum chlorofluoride catalyst. Fluorinated ketones are useful intermediates for the synthesis of various fluorinated compounds.
    Type: Grant
    Filed: June 30, 1994
    Date of Patent: October 10, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Viacheslav A. Petrov, Bruce E. Smart
  • Patent number: 5159082
    Abstract: A process for producing an aromatic compound is disclosed, which comprises coupling an aromatic sulfinic acid or a salt thereof with an aromatic halogen compound having at least one halogen atom attached to the carbon atom of the aromatic nucleus thereof or a vinyl group-containing halogen compound having at least one halogen atom attached to the carbon atom of said vinyl group in the presence of a catalyst compound containing an element selected from platinum metals.
    Type: Grant
    Filed: June 25, 1990
    Date of Patent: October 27, 1992
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Keiichi Sato, Toru Okoshi
  • Patent number: 4980511
    Abstract: Aldehydes and ketones are prepared from epoxides of the formula ##STR1## where R.sup.1 and R.sup.2 are each alkyl, alkenyl, aryl, alkoxy or aralkyl and R.sup.3 has the same meanings or is hydrogen, by a catalytic rearrangement reaction in the presence of various catalysts, in particular zeolites of the pentasil type.
    Type: Grant
    Filed: September 25, 1987
    Date of Patent: December 25, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Hoelderich, Norbert Goetz, Leopold Hupfer, Helmut Lermer
  • Patent number: 4973756
    Abstract: 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: Grant
    Filed: August 21, 1989
    Date of Patent: November 27, 1990
    Assignee: Marion Laboratories, Inc.
    Inventors: Hans Wynberg, Wolter T. Hoeve, Gerrit A. Barf, Johannes N. Koek, David R. Borcherding
  • Patent number: 4970345
    Abstract: 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: Grant
    Filed: February 20, 1986
    Date of Patent: November 13, 1990
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Masayoshi Minai
  • Patent number: 4845301
    Abstract: 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: Grant
    Filed: September 8, 1987
    Date of Patent: July 4, 1989
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Kazuo Sato, Noritsugu Yamasaki, Ichirou Takase
  • Patent number: 4814461
    Abstract: A novel process for preparing E-isomer of a triazolyl styryl ketone derivative of the formula (I): ##STR1## which includes treating Z-isomer of the derivative (which may contain E-isomer of the derivative) with sulfuric acid and an isomerization catalyst in an organic solvent, precipitating and separating the resulting sulfuric acid salt of E-isomer from the solution, and decomposing the resulting precipitate to obtain E-isomer of the derivative free from sulfuric acid. The E-isomer is useful for preparing E-isomer of triazolyl styryl carbinol of the formula (II): ##STR2## which is useful as an antimicrobial agent, a herbicide, a plant growth regulator, or the like.
    Type: Grant
    Filed: January 28, 1987
    Date of Patent: March 21, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takaharu Ikeda, Kazuhiro Tada
  • Patent number: 4814460
    Abstract: A novel process for preparing the E-isomer of triazolyl styryl ketone derivative of the formula (I): ##STR1## is disclosed. The process includes treating the Z-isomer of the derivative which may contain the E-isomer of the derivative with an acid and an isomerization catalyst in an organic solvent, precipitating and separating the resulting salt of E-isomer from the solution, and decomposing the resulting precipitate to obtain the E-isomer of the derivative free from the acid. The E-isomer is useful for preparing the E-isomer of triazolyl styryl carbinol of the formula (II): ##STR2## which is useful as an antimicrobial agent, a herbicide, a plant growth regulator, or the like.
    Type: Grant
    Filed: March 26, 1987
    Date of Patent: March 21, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takaharu Ikeda, Kazuhiro Tada, Haruki Morino
  • Patent number: 4774360
    Abstract: Enol ester precursors of benzoyl-1,3-cycloalkyldiones (e.g., the enol ester precursors of 2-(2'-nitrobenzoyl)-1,3-cyclohexanedione compounds) are converted to the desired benzoyl-1,3-cycloalkyldiones by heating the precursor in the presence of base and a catalytic amount of a trialkylsilylcyanohydrin as a cyanide source.
    Type: Grant
    Filed: June 29, 1987
    Date of Patent: September 27, 1988
    Assignee: Stauffer Chemical Company
    Inventor: Elliott Bay
  • Patent number: 4749814
    Abstract: Ethylenic carbonyl compounds of formula ##STR1## are made by the isomerization of acetylenic alcohols of formula ##STR2## in the presence of a catalyst consisting of a titanium derivative, a copper or silver derivative, and, if required, an acid, which may be in the form of an ester or anhydride, or an inorganic ester.
    Type: Grant
    Filed: April 2, 1987
    Date of Patent: June 7, 1988
    Assignee: Rhone-Poulenc Sante
    Inventor: Pierre Chabardes
  • Patent number: 4734529
    Abstract: The method for the isomerization of oxiranes of the general formula: ##STR1## wherein R.sub.1 and R.sub.3 are hydrogen; R.sub.2 is alkyl or alkylene groups of 3 to 26 carbon atoms or the phenyl group which may also be substituted, and R.sub.4 is hydrogen or alkyl from 1 to 26 carbon atoms and in which the carbon atoms of the epoxy ring can also form components of a cyclic system, wherein as a catalyst there is used alkali iodide and a polyethyleneglycol with an average mol mass of 400 to 10,000 with a boiling point, preferably above the boiling point of the carbonyl compounds that are formed.
    Type: Grant
    Filed: December 22, 1986
    Date of Patent: March 29, 1988
    Assignee: Degussa Aktiengesellschaft
    Inventors: Marion Berg, Andreas Grund, Guenter Prescher
  • Patent number: 4731482
    Abstract: Process for the preparation of phenylpropanones having formula: ##STR1## R and R.sub.1, equal or different, being C.sub.1 -C.sub.4 alkyl groups or being coincident in the CH.sub.2 group of a heterocyclic ring, wherein the corresponding allylbenzenes are catalytically epoxidized by means of H.sub.2 O.sub.2, in a biphase system comprising an aqueous phase containing H.sub.2 O.sub.2 and an organic phase containing said allylbenzenes, a solvent immiscible with said aqueous phase and a catalyst having formula Q.sub.3 XW.sub.4 O.sub.24 (Q being a quaternary cation containing hydrocarbylic groups having on the whole from 20 to 70 C atoms, and X being P or As) and wherein the thus obtained epoxides are isomerized by heating at 90.degree.-150.degree. C., in the presence of catalytic amounts of LiI.
    Type: Grant
    Filed: October 17, 1986
    Date of Patent: March 15, 1988
    Assignee: Montedison S.p.A.
    Inventors: Carlo Venturello, Rino D'Aloisio, Marco Ricci
  • Patent number: 4695673
    Abstract: An acylated 1,3-dicarbonyl compound is produced by rearrangement of the corresponding enol ester in the presence of a cyanide source. In one embodiment the cyanide source is employed with a molar excess of a moderate base, with respect to the enol ester. In another embodiment, the cyanide source is a stoichiometric amount, with respect to the enol ester, of potassium or lithium cyanide and a catalytic amount of a crown ether is used.
    Type: Grant
    Filed: June 9, 1986
    Date of Patent: September 22, 1987
    Assignee: Stauffer Chemical Company
    Inventors: James B. Heather, Pamela D. Milano
  • Patent number: 4694107
    Abstract: Ketones are prepared by isomerization of aldehydes at elevated temperatures over zeolites.
    Type: Grant
    Filed: July 2, 1986
    Date of Patent: September 15, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Hoelderich, Franz Merger, Wolf D. Mross, Rolf Fischer
  • Patent number: 4540825
    Abstract: A method for producing 2-cyclopentenones represented by the formula, ##STR1## wherein R represents an alkyl, alkenyl, cycloalkyl, substituted or non-substituted aryl or aralkyl group, which comprises heating 4-cyclopentenones represented by the formula, ##STR2## wherein R has the same meaning as above, in the presence of 1,8-diaza-bicyclo[5,4,0]undecene or its organic acid salt.The 2-cyclopentenones are useful as an intermediate for perfumes, medicines and agricultural chemicals.
    Type: Grant
    Filed: April 2, 1984
    Date of Patent: September 10, 1985
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Katsuyuki Shiota, Kunihiko Tanaka, Masayoshi Minai
  • Patent number: 4537995
    Abstract: A process of isomerizing branched aldehydes to ketones is provided which comprises contacting at isomerization conditions a branched aldehyde with a zeolite catalyst of the formula: ##EQU1## wherein M is selected from the group consisting of a mixture of alkali metal cations, especially sodium, and tetraalkylammonium cations, the alkyl groups of which preferably contain 2 to 5 carbon atoms, and x is at least 5. The contacting is conducted at a temperature of from about 200.degree. C. to about 600.degree. C. and at a pressure of from about 20 psig to about 100 psig. The branched aldehyde is contacted in the presence of water in a molar ratio of water-to-aldehyde of up to about 20 to 1.
    Type: Grant
    Filed: November 7, 1983
    Date of Patent: August 27, 1985
    Assignee: Celanese Corporation
    Inventors: H. Clay Linstid, III, Gerald S. Koermer
  • Patent number: 4510329
    Abstract: A process for preparing cyclopentenolones of the formula ##STR1## wherein R.sub.1 is an alkyl group having not more than 6 carbon atoms, an alkenyl or alkynyl group having not more than 6 carbon atoms or a group of the formula: ##STR2## in which R.sub.2 is a hydrogen atom, a methyl group or a halogen atom directly from the corresponding furan-carbinols of the formula: ##STR3## wherein R.sub.1 is as defined above in a single step with an excellent yield, characterized in that the furan-carbinols are treated with water in the presence or absence of a catalyst.
    Type: Grant
    Filed: November 28, 1980
    Date of Patent: April 9, 1985
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kenji Saito, Hiroshi Yamachika
  • Patent number: 4380672
    Abstract: 2-phenyl propanal is converted to 2-indanone by contact at conversion conditions, typically vapor-phase conditions, with a catalyst of the formula Mo.sub.12 Cu.sub.0.1-10 V.sub.0.1-5 W.sub.0.1-3 M.sub.0-3 O.sub.x where M is an optional promoter, such as Sn, Sb, Te or a Group VIII element.
    Type: Grant
    Filed: February 2, 1982
    Date of Patent: April 19, 1983
    Assignee: The Standard Oil Company
    Inventors: Louis J. Velenyi, Andrew S. Krupa
  • Patent number: 4371711
    Abstract: A method of producing a 4-hydroxycyclopentenone represented by the formula, ##STR1## wherein R.sub.1 is an alkyl, alkenyl, alkynyl, cycloalkyl, thienyl, phenyl, p-methylbenzyl or benzyl group and R.sub.2 is an alkyl, alkenyl or alkynyl group having 6 or less carbon atoms, which comprises reacting a furylcarbinol compound of the formula, ##STR2## wherein R.sub.1 is as defined above, in the presence of an acid in a mixed solvent of water and an organic solvent, to obtain a cyclopentenone compound of the formula, ##STR3## wherein R.sub.1 is as defined above; reacting the cyclopentenone compound in the presence of an oxidizing agent to obtain a cyclopentendione compound of the formula, ##STR4## wherein R.sub.1 is a defined above; reacting the cyclopentendione compound with a Grignard reagent of the formula,R.sub.2 MgXwherein R.sub.2 is as defined above and X is chlorine, bromine or iodine atom, to obtain an oxocyclopentene compound of the formula, ##STR5## wherein R.sub.1 and R.sub.
    Type: Grant
    Filed: May 20, 1980
    Date of Patent: February 1, 1983
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kenji Saito, Hiroshi Yamachika
  • Patent number: 4347386
    Abstract: A process for preparing cyclopentenolones in good yields which comprises treating a 4-hydroxy-4-R.sub.2 -5-R.sub.1 -2-cyclopentenone of the formula: ##STR1## wherein R.sub.1 is an alkyl group having not more than 6 carbon atoms, an alkenyl group having not more than 6 carbon atoms, an alkynyl group having not more than 6 carbon atoms or a group of the formula: ##STR2## (in which R.sub.3 is hydrogen, methyl or halogen) and R.sub.2 is a hydrogen atom or a methyl group, provided that when R.sub.2 is hydrogen, R.sub.1 is neither .alpha.-methylallyl nor .alpha.-methylpropargyl, in an aqueous medium in the presence or absence of a metal salt at a temperature of 20.degree. to 200.degree. C. to give the corresponding 2-R.sub.1 -3-R.sub.2 -4-hydroxy-2-cyclopentenone of the formula: ##STR3## wherein R.sub.1 and R.sub.2 are each as defined above.
    Type: Grant
    Filed: April 22, 1981
    Date of Patent: August 31, 1982
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kenji Saito, Hiroshi Yamachika
  • Patent number: 4329506
    Abstract: Aldehydes, such as isobutyraldehyde, are isomerized to ketones, such as methyl ethyl ketone, by contact at isomerization conditions, typically vapor-phase conditions, with a catalyst of the formula M.sub.0.15-15 M'.sub.0.05-12 O.sub.x where M is at least one of Mo and Cu and M' is a promoter, such as a Group IIB or VIII element.
    Type: Grant
    Filed: August 28, 1980
    Date of Patent: May 11, 1982
    Assignee: The Standard Oil Company
    Inventors: Louis J. Velenyi, Andrew S. Krupa
  • Patent number: 4252818
    Abstract: 7-[3-(4-Acetyl-3-hydroxy-6-iodo-2-propylphenoxy)-2-hydroxypropoxy]-4-oxo-8- propyl-4H-1-benzopyran-2-carboxylic acid and its pharmaceutically acceptable salts are employed as antagonists of SRS-A (the slow reacting substance of anaphylaxis) in the treatment of asthma and allergic diseases.
    Type: Grant
    Filed: August 2, 1979
    Date of Patent: February 24, 1981
    Assignee: Merck & Co., Inc.
    Inventors: Joshua Rokach, Pierre A. Hamel, Ralph F. Hirschmann