Processing

Please wait...

Settings

Settings

Goto Application

1. EP0775102 - PROCESS FOR OBTAINING UNSATURATED CYCLOALIPHATIC KETONES

Office European Patent Office
Application Number 96913678
Application Date 28.05.1996
Publication Number 0775102
Publication Date 28.05.1997
Publication Kind B1
IPC
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; Ketonic chelates
587Unsaturated compounds containing a keto group being part of a ring
647having unsaturation outside the ring
C07B 61/00
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
61Other general methods
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 45/67
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 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 carboxyl 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
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 & CIE
Inventors NAEF FERDINAND
DECORZANT RENE
Priority Data 167695 08.06.1995 CH
9600499 28.05.1996 IB
Title
(DE) VERFAHREN ZUR HERSTELLUNG VON UNGESÄTTIGTEN CYCLOALIFATISCHEN KETONEN
(EN) PROCESS FOR OBTAINING UNSATURATED CYCLOALIPHATIC KETONES
(FR) PROCEDE POUR L'OBTENTION DE CETONES CYCLOALIPHATIQUES INSATUREES
Abstract
(EN)
The invention concerns cycloaliphatic ketones of formula (I) which have two conjugated double bonds in positions 1 and 3, or 2 and 4, as shown by the dashed lines, and in which formula R defines a C1-C3 alkyl radical. The cycloaliphatic ketones are used as intermediate products in the preparation of jasmonic derivatives and are obtained by an addition reaction between cyclopentanone and an aldehyde of formula (II) of which the double bond has the configuration (E) and in which R has the meaning given above, to provide a dienic cyclopentanone of formula (Ia) E,E. The resulting cyclopentanone is optionally subjected to a heat treatment to give a cyclopentenone of formula (Ib) Z. 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, 2-(1'Z)-pent-1'-enyl-cyclopent-2-enone, dimethyl [2-(pent-(1'Z)-enyl)-3-oxo-1-cyclopentyl]-malonate malonic esters and dimethyl [2-(but-(1'Z)-enyl)-3-oxo-1-cyclopentyl]-malonate malonic esters are novel chemical compounds.

(FR)
Les cétones cycloaliphatiques de formule (I) possédant deux doubles liaisons conjugées dans les positions 1 et 3, ou 2 et 4, telles qu'indiquées par les pointillés, et dans laquelle R sert à définir un radical alkyle de C1 à C3, produits intermédiaires utiles pour la préparation de dérivés jasmoniques, sont obtenues par une réaction d'addition entre la cyclopentanone et un aldéhyde de formule (II), dont la double liaison est de configuration (E) et dans laquelle R a le sens indiqué ci-dessus, pour fournir une cyclopentanone diénique de formule (Ia) E,E et l'on soumet, le cas échéant, la cyclopentanone ainsi formée à un traitement thermique pour donner une cyclopenténone de formule (Ib) Z. Les 2-(E,2'Z)-but-2'-énylidène-cyclopentanone, 2-(1'Z)-but-1'-ényl-cyclopent-2-énone, 2-(E,2'E)-pent-2'-énylidène-cyclopentanone, 2-(Z,2'E)-pent-2'-énylidène-cyclo-pentanone et 2-(1'Z)-pent-1'-ényl-cyclopent-2-énone, ainsi que les esters maloniques [2-(pent-(1'Z)-ényl)-3-oxo-1-cyclopentyl]-malonate de diméthyle et [2-(but-(1'Z)-ényl)-3-oxo-1-cyclopentyl]-malonate de diméthyle, sont des entités chimiques nouvelles.