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1. US5760277 - Process for the manufacture of unsaturated cycloaliphatic ketones

Office United States of America
Application Number 08765801
Application Date 15.01.1997
Publication Number 5760277
Publication Date 02.06.1998
Grant Number 5760277
Grant Date 02.06.1998
Publication Kind A
IPC
C07C 67/32
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
67Preparation of carboxylic acid esters
30by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
317by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
32Decarboxylation
C07B 61/00
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
61Other general methods
C07C 45/00
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
45Preparation of compounds having C=O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
C07C 45/67
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
45Preparation of compounds having C=O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
61by reactions not involving the formation of C=O groups
67by isomerisation; by change of size of the carbon skeleton
C07C 45/74
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
45Preparation of compounds having C=O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
61by reactions not involving the formation of C=O groups
67by isomerisation; by change of size of the carbon skeleton
68by increase in the number of carbon atoms
72by reaction of compounds containing C=O groups with the same or other compounds containing C=O groups
74combined with dehydration
C07C 49/00
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
49Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
CPC
C07C 69/738
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
69Esters of carboxylic acids; Esters of carbonic or haloformic acids
66Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
73of unsaturated acids
738Esters of keto-carboxylic acids ; or aldehydo-carboxylic acids
C07C 45/67
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
45Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
61by reactions not involving the formation of >C = O groups
67by isomerisation; by change of size of the carbon skeleton
C07C 45/74
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
45Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
61by reactions not involving the formation of >C = O groups
67by isomerisation; by change of size of the carbon skeleton
68by increase in the number of carbon atoms
72by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
74combined with dehydration
C07C 49/647
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
49Ketones; Ketenes; Dimeric ketenes
587Unsaturated compounds containing a keto groups being part of a ring
647having unsaturation outside the ring
Applicants Firmenich SA
Inventors Naef Ferdinand
Decorzant Rene
Agents Pennie & Edmonds LLP
Priority Data 00167695 08.06.1995 CH
Title
(EN) Process for the manufacture of unsaturated cycloaliphatic ketones
Abstract
(EN)

The cycloaliphatic ketones of formula ##STR1## having two conjugated double bonds in positions 1 and 3, or 2 and 4, such as indicated by the dotted lines, and wherein R defines a C.sub.1 to C.sub.3 alkyl radical, usefuil intermediate products for the preparation of jasmonic derivatives, are prepared by an addition reaction btween the cyclopentanone and an aldehyde of formula ##STR2## wherein the double bond is of (E) configuration and wherein R has the meaning indicated above, to provide a diene cyclopentanone of formula ##STR3## and, optionally, in that the cyclopentanone thus formed is subjected to a thermal treatment to provide a cyclopentenone of formula ##STR4## The 2-(E,2'Z)-but-2'-enylidene-cyclopentanone, 2-(1'Z)-but-1'-enyl-cyclopent-2-enone, 2-(E,2'E)-pent-2'-enylidene-cyclopentanone, 2-(Z,2'E)-pent-2'-enylidene-cyclopentanone and 2-(1'Z)-pent-l'-enyl-cyclopent-2-enone, as well as the malonic esters dimethyl 2-(pent-(1'Z)-enyl)-3-oxo-1-cyclopentyl!-malonate and dimethyl 2-(but-(1'Z)-enyl)-3-oxo-1-cyclopentyl!-malonate, are novel chemical entities.