4-Vinyl guaiacol acetate (4-VG-Ac), a renewable styrene type monomer, was synthesized from from vanillin in a telescoping reaction, allowing satisfactory yields and a straightforward single purification step. The monomer bears much synthetic potential, as a simple post-polymerization deprotection step would allow for pending phenyl groups to be exploited for post-functionalization.
4-VG-Ac was then tested towards Atom Transfer Radical Polymerization (ATRP), achieving good monomer conversion and control in its Supplementary Activator and Reducing Agent (SARA) variant. Optimization required the evaluation of various reaction parameters and their effect on the polymerization system, leading to optimal choice of solvent, catalytic system and initiator. The use of highly active chloride-based ATRP initiators and CuCl2/TMPA catalytic system played a major role in establishing control over the polymerization.