Organic compositions and their manufacture

Details Organic compositions and their manufacture Organic compositions and their manufacture

1993-05-20

1994-03-15

Prescott, Arthur C.

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

Organic compounds

Carboxylic acid esters

560 55, 560 56, 560125, 560185, 549 79, 549505, 544335, 544336, 544353, 548236, C07C32100

Patent

active

052947335

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

REFERENCES:
patent: 3997590 (1976-12-01), Lester
patent: 4940813 (1990-07-01), Corley et al.
Seebach, D. et al., Helv. Chim. Acta, 71(1) 155-167 (1988).

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