GB803567A - A process for the production of 1-ketocyclo-octyl-2-methylene compounds - Google Patents

Abstract

1-Ketocyclo octyl 4-methylene compounds of general formula <FORM:0803567/IV (b)/1> where X is nitrile carboxylic acid group or alkali metal salt thereof are prepared by reacting a tertiary 2-amino-methyl cyclo octanone (1) in the form of its salts or quaternization products thereof, with an alkali metal cyanide and if desired saponifying the resultant 2-(cyanomethyl)-cyclo-octanone (1). The tertiary 2-aminomethyl cyclo octanone (1) may be prepared by the Mannich reaction using cyclo-octanone with formaldehyde and secondary amines, e.g. dimethylamine, diethylamine, methylethylamine, pyrrolidine, piperidine or morpholine. The quaternization product or salt may then be obtained e.g. by reacting with hydrogen chloride, bromide or iodide or with methyl or ethyl bromide or iodide or with dimethyl sulphate or para toluene sulphonic acid ethyl ester. The reaction of these compounds with the alkali cyanides is preferably carried out in aqueous or aqueous alcoholic solution at 50 DEG to 80 DEG C. with excess sodium or potassium cyanide. The saponification of the nitrile is preferably effected by heating with aqueous caustic alkali solution and the 1-ketocyclo octyl 2-acetic acid is obtained from its salt by neutralization with hydrochloric or sulphuric acid. Examples are given for the preparation of 2-(cyanomethyl) cyclo octanone-(1) and 1-ketocyclo octyl-2-acetic acid from sodium cyanide and (1) 2-dimethylaminomethylcyclo octanone - (1) iodomethylate; (2) 2-trimethyl ammonium methyl-cyclo octanone-(1) methyl sulphate; (3) 2-dimethyl aminomethyl cyclo-octanone-(1) hydrochloride; (4) 2-piperidinomethylcyclo-octanone-(1) iodomethylate.