Preparation of all the possible ring-deuteriated benzoic acids by reductive dehalogenation of the corresponding halogenobenzoic acids with raney alloys in an alkaline deuterium oxide solution

Abstract

All the possible undeuteriated benzoic acids were prepared mainly by treatment of the corresponding bromobenzoic acid with Raney Cu–Al alloy in 10% NaOD–D₂O solution. [2,3,4,5,6-²H₅] Benzoic acid was obtained from pentafluorobenzoic acid by a similar reaction. However, only [2,3,4,5-²H₄] benzoic acid was prepared by decarboxylation of [2,3,4,5-²H₄] phthalic acid.