Preparation of cyclohexanedione derivatives

Details Preparation of cyclohexanedione derivatives Preparation of cyclohexanedione derivatives

C - Chemistry, Metallurgy

07

C

260/295, 260/328

C07C 49/703 (2006.01) C07C 45/67 (2006.01) C07D 213/50 (2006.01) C07D 309/06 (2006.01) C07D 309/22 (2006.01) C07D 335/02 (2006.01)

Patent

CA 1280756

ABSTRACT OF THE DISCLOSURE: Disclosed is a process for the preparation of cyclohexanedione derivatives of the general formula I Image (I) where R1 is C2-C8-alkyl, C2-C8-alkenyl, C3-C12-cycloalkyl, C5-C12-cycloalkyl with 0-4 olefinically unsaturated bonds, C2-C8-alkylthioalkyl, C6-C12-bicyclo-alkyl 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, and R2 is alkyl of not more than 6 carbon atoms. The process comprises reacting an .alpha. , .beta.-unsaturated ketone of formula (II): (II) Image with a dialkyl malonate in the presence of a base to give a alkoxycarbonylcyclohexenolone or a salt thereof, and subjecting the obtained product to acylation, hydrolysis and decarboxylation, The .alpha. , .beta.-unsaturated ketone (II) is reacted 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.

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