Process for the preparation of cyclohexanedionecarboxylic acid d

Details Process for the preparation of cyclohexanedionecarboxylic acid d Process for the preparation of cyclohexanedionecarboxylic acid d

1987-01-29

1989-02-07

Killos, Paul J.

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

Organic compounds

Chalcogen in the nitrogen containing substituent

544172, 546237, 546238, 548539, 556117, 558414, 560116, 560118, 560125, 560126, 562500, 562507, 562508, C07D27910, C07C 6722

Patent

active

048032689

ABSTRACT:
The present invention relates to a novel, optimized process for the preparation of cyclohexanedionecarboxylic acid derivatives of formula I which can be carried out in a single vessel affording a very good yield, which process comprises heating a reactive carboxylic acid derivative of formula III ##STR1## wherein X is a halide, an alkylsulfonic or arylsulfonic acid radical or the molecular radical ##STR2## which is necessary to form an anhydride and R.sub.1 is alkyl or cycloalkyl, with an alkali metal cyanide or copper cyanide, in an inert organic solvent, to give a mixture, then adding in succession to said mixture, at a temperature in the range from 0.degree. C. to room temperature, zinc chloride, an equimolar amount, with respect to the carboxylic acid derivative of formula III, of a 3,5-cyclohexanedione-1-carboxylic acid derivative of formula II ##STR3## wherein A is an ester or amide radical, and, dropwise, an amine, and, after acidifying the reaction mixture with an aqueous acid, isolating the resultant 4-acyl-3,5-cyclohexanedione-1-carboxylic acid derivative of formula I ##STR4## by extraction. Said cyclohexanedionecarboxylic acid derivatives have herbicidal and plant growth regulating properties.

REFERENCES:
patent: 4440566 (1984-04-01), Luo
patent: 4560403 (1985-12-01), Motojima et al.
patent: 4618360 (1986-10-01), Brunner
patent: 4623382 (1986-11-01), Brunner

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