Organic compositions and their manufacture

Abstract

Preparation of cyclohexanediones of the formula ##STR1## are disclosed. An aldehyde of the formula R--CHO is reacted with a ketene type compound of the formula (R.sub.1) (R.sub.2) C.dbd.C.dbd.O to give a polymer: ##STR2## wherein n ranges from about 2 to about 1,000. The polymer is hydrolyzed to produce a mixture of an unsaturated acid of the formula R--CH.dbd.C(R.sub.1)--COOH and a hydroxy ester or acid of the formula R--CH(OH)C(R.sub.1) (R.sub.2)--COOR.sub.3, the acids in the mixture are converted for esters. The hydroxy ester of the ester mixture is converted to unsaturated ester of the formula R--CH.dbd.C(R.sub.1)--COOR.sub.3. The unsaturated ester is contacted with a basic catalyst to cyclize it to the cyclic dione ester of the formula ##STR3## and this ester is then hydrolyzed and decarboxylated to give the product ##STR4## wherein: R is selected, e.g., from alkylthio, alkylthioalkyl, cycloalkyl, alkyl substituted cycloalkyl, alkoxy, alkanoyloxy, alkoxycarbonyl, aryl, substituted aryl, heterocylcic, or substituted heterocyclic, wherein each group or moiety has up to 20 carbons; and R.sub.1, R.sub.2 and R.sub.3 are each selected, e.g., from alkyl or cycloalkyl of up to 20 carbons, and R.sub.2 and R.sub.3 can also be hydrogen.

Dependencies are inferred from the claim text.