Carbonyl Of Aldehyde Or Ketone Reacted To Form Oxirane Ring Patents (Class 549/519)
  • Patent number: 4988829
    Abstract: A process for making the known fungicide intermediate 2-(4-chlorophenyl ethyl)-2-tert.-butyloxirane of the formula ##STR1## comprising (a) mixing a solution of trimethylsulphonium bromide of the formula(CH.sub.3).sub.3 S.sup..sym. Br.sup..crclbar. (II)in a methanol/toluene mixture with preheated toluene and simultaneously distilling off a methanol/toluene mixture at a temperature between 65.degree. and 110.degree. C. until a suspension having a solids content between 10 and 70% by weight is formed, and(b) reacting the suspension of trimethylsulphonium bromide in toluene thus obtained with 1-(4-chlorophenyl)-4,4-dimethylpentan-3-one of the formula ##STR2## in the presence of solid potassium hydroxide, diethylene glycol and water at a temperature between 20.degree. and 120.degree. C.
    Type: Grant
    Filed: June 30, 1989
    Date of Patent: January 29, 1991
    Assignee: Bayer Aktiengessellschaft
    Inventors: Paul Fiedler, Martin Littmann, Manfred Lenthe, Achim Noak, Gerd Siekmann
  • Patent number: 4980485
    Abstract: Optically active periplanone-B is manufactured through oxidizing (1RS, 4S, 5E)-isopropyl-7-methylene-5-cyclodecene-1-ol. The oxidized product is regioselectively enolized and then sulfenylated. The sulfenylated product is oxidized and then subjected to decomposition of the sulfoxide. The decomposed product is epoxidated, and the epoxidated product is converted into an enolate which is then oxidized. The oxidized product is oxidized and then regio- and stereoselectively epoxidated to obtain optically active periplanone-B.
    Type: Grant
    Filed: September 26, 1989
    Date of Patent: December 25, 1990
    Assignee: Japan Tobacco Inc.
    Inventors: Kenji Mori, Takeshi Kitahara, Koshi Koseki
  • Patent number: 4960911
    Abstract: A process for the preparation of oxiranes is disclosed in which a ketone of the formula ##STR1## wherein Y represents chlorine or phenyl, X represents oxygen or CH.sub.2 and Z represents hydrogen or halogen is reacted with trimethylsulphonium methyl sulphate formed by treating dimethyl sulphide with dimethyl sulphate. The process is carried out in the presence of potassium hydroxide or sodium hydroxide powder in an inert organic diluent at 0.degree. to 60.degree. C. The products are useful as intermediates for the formation of plant growth regulants and fungicides.
    Type: Grant
    Filed: October 28, 1988
    Date of Patent: October 2, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rudolf Zerbes, Siegfried W. Linke, Karl H. Mohrmann, Wolf Reiser
  • Patent number: 4933477
    Abstract: Phenyl-substituted epoxides of the formula ##STR1## where R.sup.1 and R.sup.2 are each hydrogen, alkyl, alkenyl, phenyl, halogen, nitro, alkoxy, haloalkyl, phenoxy or phenylsulfonyl, are prepared by reducing a haloacetophenone to a halohydrin and reacting the halohydrin with an alkali metal hydroxide by a process in which the reduction with the alkali metal borohydride and the reaction are carried out in aqueous organic solution, or the cyclization of a halohydrin with an alkali metal hydroxide is carried out in an organic liquid.
    Type: Grant
    Filed: August 25, 1988
    Date of Patent: June 12, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Norbert Goetz, Hans-Gert Recker, Hubert Smuda
  • Patent number: 4929735
    Abstract: A process for the preparation of an oxirane of the formula ##STR1## in which X is 4-chlorobenzyl, 4-phenylphenoxy or 1H-(1,2,4)-triazolyl,comprising reacting dimethyl sulphate with an excess of dimethyl sulphide thereby to form trimethylsulphonium methyl-sulphate of the formula(CH.sub.3).sub.3 S.sym.CH.sub.3 SO.sub.4 .crclbar.,and without prior isolation reacting the trimethylsulphonium methyl-sulphate with a keytone of the formula ##STR2## in the presence of solid potassium hydroxide or sodium hydroxide in dimethyl sulphide at a temperature between 0.degree. C. and 50.degree. C.
    Type: Grant
    Filed: April 22, 1988
    Date of Patent: May 29, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolf Reiser, Peter Feyen
  • Patent number: 4898954
    Abstract: A process for the preparation of oxiranes is disclosed in which trimethylsulphonium methyl sulphate, formed by treating dimethyl sulphide with dimethyl sulphate in the presence of tert.-butanol, is reacted, without previous isolation, with a ketone in the presence of a base and in the presence of tert.-butanol. The resultant oxiranes are useful in the preparation of plant growth regulants and fungicides.
    Type: Grant
    Filed: September 3, 1985
    Date of Patent: February 6, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl H. Mohrmann, Wolf Reiser, Siegfried W. Linke, Rudolf Zerbes
  • Patent number: 4886892
    Abstract: A process for the preparation of oxiranes is disclosed in which a ketone of the formula ##STR1## wherein Y represents chlorine or phenyl, X represents oxygen or CH.sub.2 and Z represents hydrogen or halogen is reacted with trimethylsulphonium methyl sulphate formed by treating dimethyl sulphide with dimethyl sulphate. The process is carried out in the presence of potassium hydroxide or sodium hydroxide powder in an inert organic diluent at 0.degree. to 60.degree. C. The products are useful as intermediates for the formation of plant growth regulants and fungicides.
    Type: Grant
    Filed: January 27, 1987
    Date of Patent: December 12, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rudolf Zerbes, Siegfried W. Linke, Karl H. Mohrmann
  • Patent number: 4632999
    Abstract: A process for the preparation of an oxirane of the formula ##STR1## in which Y represents chlorine or phenyl, X represents oxygen or Ch.sub.2 and Z represents hydrogen or halogen, which comprises containing dimethyl sulphoxide with dimethyl sulphate whereby to form trimethyloxosulphonium methyl sulphate of the formula(CH.sub.3).sub.3 SO.sup..sym. CH.sub.3 SO.sub.4.sup.63 (II)and thereafter, without isolating said trimethyloxosulphonium methyl sulphate, contacting the same with a ketone of the formula ##STR2## in which X, Y and Z have the meanings indicated above, in the presence of a base and in the presence of an inert organic diluent, at a temperature between 0.degree. C. and 60.degree. C.
    Type: Grant
    Filed: October 22, 1985
    Date of Patent: December 30, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rudolf Zerbes, Siegfried W. Linke, Karl H. Mohrmann, Wolf Reiser
  • Patent number: 4499294
    Abstract: An improved process for producing the hypoglycemic compound, methyl 2-tetradecylglycidate, by reacting methyl .alpha.-chloropalmitate with lithium methoxide in the presence of formaldehyde in a dipolar aprotic solvent such as DMF or DMSO.
    Type: Grant
    Filed: January 21, 1983
    Date of Patent: February 12, 1985
    Assignee: McNeilab, Inc.
    Inventor: Cynthia A. Maryanoff