Syntheses of Polymerizable Acetals. I. Vinylbenzaldehyde Acetals with Perfume Alcohols

Several acetal monomers and a hemiacetal monomer of vinylbenzaldehydes were synthesized from the reaction with some perfume alcohols in the presence of p-toluenesulfonic acid as an acid catalyst. It was found that primary alcohols such as citronellol and geraniol with the exception of cinnamyl alcohol afforded acetal monomers in high yields, secondary alcohols such as borneol and menthol in low yields, with the latter affording only hemiacetal monomer, and linalool, a tertiary alcohol, neither acetal nor hemiacetal monomers. The radical polymerizations of the acetal and hemiacetal monomers synthesized provided soluble polymers which easily release perfume alcohols under mild acidic conditions.