Anodic methoxylation of cinnamate esters

the present work describes the electrochemical oxidation of methyl cinnamate ring methoxylated derivatives in neutral or basic methanolic solution. in the electrochemical studies cyclic voltammetry and preparative electrolyses under controlled potential or current conditions in divided or undivided cells were used. the influence of current density, cell type, electrode material, solvent, substrate and base concentration was investigated for methyl 4-methoxycinnamate.the products result from aromatic ring and side chain methoxylation, however, nuclear methoxylation products were observed in higher yields when the number of methoxy groups in the aromatic ring was increased. the structure of the products is dependent on the work-up procedures.