Insoluble Lignin Models (V): Preparation and Alkaline Condensation Reactions of a Polymer-Bound Quinone Methide

Abstract

A lignin model, capable of forming a quinone methide in alkali, was bound to polystyrene and heated in alkali with 2,6-dimethoxyphenol. The polymer-supported phenol did not react with the soluble phenol under a variety of conditions, while an analogous non-bound phenol rapidly reacted with 2,6-dimethoxyphenolate ion, giving a condensation dimer in good yield. Condensation in the two-phased system appeared to be inhibited primarily by steric factors involving the supporting polystyrene resin.