Preparation of cyclohexane-dione derivatives

Details Preparation of cyclohexane-dione derivatives Preparation of cyclohexane-dione derivatives

1990-08-02

1992-06-02

Rotman, Alan L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Sulfur containing

568 13, 568329, 568340, 568346, 568367, 568374, 568375, 568376, 568377, 568378, 568427, 546342, C07C 4500, C07C 4921, C07C32304, C07C32114

Patent

active

051188562

ABSTRACT:
A process for the preparation of cyclohexanedione derivatives of the general formula I ##STR1## where R.sup.1 is C.sub.2 -C.sub.8 -alkyl, C.sub.2 -C.sub.8 -alkenyl, C.sub.3 -C.sub.12 -cycloalkyl, C.sub.5 -C.sub.12 -cycloalkyl with 0-4 olefinically unsaturated bonds, C.sub.2 -C.sub.8 -alkylthioalkyl, C.sub.6 -C.sub.12 -bicycloalkyl with 0-3 olefinically unsaturated bonds, unsubstituted or substituted aryl or hetaryl, or a heterocyclic radical of 4 to 7 atoms of which not more than 3 may be hetero-atoms chosen from O, S and N, the radical being saturated or olefinically unsaturated, by reacting an .alpha.,.beta.-unsaturated ketone (II) with a dialkyl malonate in the presence of a base to give the alkoxycarbonylcyclohexenolone or its salt (III) ##STR2## and acylation, hydrolysis and decarboxylation of (III), wherein the .alpha.,.beta.-unsaturated ketone (II) is reacted, in the presence of a base, with the dialkyl malonate in a solvent from which the alcohol liberated from the malonate can be distilled off, the alcohol is distilled off, where appropriate as an azeotrope, the salt of the alkoxycarbonylcyclohexenolone is reacted with a carboxylic acid halide and the product, where appropriate after removal of excess acyl halide, is treated with an acylation catalyst, hydrolyzed and decarboxylated.

REFERENCES:
patent: 3950420 (1976-04-01), Sawaki et al.
patent: 4115204 (1978-09-01), Murtha
patent: 5006158 (1991-04-01), Carter et al.

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