Reactions of co-ordinated ligands. Part 8. Reaction of Grignard reagents with 2-alkoxy-1,3-dioxolans; an improved route to aldehydes

Abstract

The yields of 2-phenyl-1,3-dioxolan obtained from phenylmagnesium bromide and 2-alkoxy-1,3-dioxolans in which the alkoxy-group is of the type Me[O·CH₂·CH₂]_n–O increase as the value of n proceeds along the series 4,3,1,2. Several Grignard reagents (including phenylmagnesium bromide) react with the 2-alkoxy-1,3-dioxolan in which n= 2 to give the expected 2-substituted-l,3-dixolans, whose yields are considerably higher than those of the diethyl acetals obtained from the corresponding reaction with ethyl orthoformate.