Preparation of deuteriated 1-phenylethanols by reductive dehalogenation of the corresponding halogenoacetophenones with Raney alloys in an alkaline deuterium oxide solution

Abstract

Deuteriated 1-phenylethanols were prepared by reductive dehalogenation of the corresponding halogenoacetophenones with Raney Ni–Al and Cu–Al alloys in 5% NaOD–D₂O solution. It was found that the Ni–Al alloy introduced greater than expected numbers of deuterium atoms in the phenyl ring, but the expected deuteriated 1-phenylethanols were obtained in high yield and in high isotopic purity when Raney Cu–Al alloy was used.