Reformatsky reactions with o- and p-substituted benzophenones

Abstract

Nine new β,β-diarylhydracrylic acids are reported from the condensation of monosubstituted benzophenones with ethyl bromoacetate in Reformatsky reactions. The reaction of 4-nitrobenzophenone which fails to go into classical Reformatsky reactions can be accomplished in excellent yield by the two-step process; however, 2-nitrobenzophenone fails to react under any conditions.In the case of 2-chlorobenzophenone in benzene–toluene, the hydracrylic acid is not isolated, but rather the unsaturated β-chlorophenyl-β-phenyacrylic acid. Diethyl ether appeared in general to be superior to benzene–toluene as a solvent for the reactions. Anisole under reduced pressure has also been used successfully in two cases.