Reduction by dissolving metals. XXII. Reduction and reductive alkylation of some Methoxy- and Dimethylamino-benzoic acids

Abstract

Reductions by lithium in ammonia of 2-, 3- or 4-methoxy- or 2- or 4- dimethylamino-benzoic acids result in total loss of 4-OMe and 4-NMe2, and partial loss of 2-OMe. In the presence of methanol loss of 2-OMe is minimized. Intermediate dianions can be alkylated to the corresponding 1-alkyl-1,4-dihydrobenzoic acids which in some cases are useful intermediates in synthesis. A useful new procedure for synthesizing 2- alkylcyclohex-2-enones is described.