Chloromethylated polystyrene was reacted with vanillin under phase transfer catalyzed conditions. This reaction was performed under different conditions, including variations of the phase transfer catalysts, the reaction solvent, the type of base, the reaction time and temperature. In addition, the effect of the reaction technique (i.e., solid-liquid-liquid and solid-liquid-solid systems) on the reaction conversion was studied. Polymer-supported vanillin was evaluated for its utilization in polymer analogue conversions by performing condensation reactions of the aldehyde functionality with malononitrile, ethyl cyanoacetate, cyanoacetamide, cyanothioacetamide, 2-aminophenol, hydrazine hydrate and hydroxylamine hydrochloride. In all cases, the reactions were followed up by means of FTIR spectroscopic analysis. (C) 2002 Published by Elsevier Science B.V.