Insoluble Lignin Models (3): Preparation of a Polymer-Bound Guaiacylpropanol Model

Guaiacylpropanol (4), has been attached at the gamma carbon through a benzyl ether linkage to a macroreticular polystyrene resin. The phenolic site of 4 was protected as an allyl ether when coupled to the resin. The amount of lignin model 4 which was attached to the polymer was determined by cleaving the benzyl ether linkage with iodotrimethlsilane (ITS) and quantifying the amount of released guaiacylpropanol. The ITS method was reproducible but not quantitative due to a high model loading (1.29 mmol/g). Both FTIR and 13 C-NMR were used to characterize the insoluble model.