A unique lignin model dimer, 2-(2-methoxyphenoxy)-1-(3-methoxy-4-hydroxyphenyl)-1,5-pentanediol (8), was attached to a macroreticular polystyrene resin by means of a trityl ether linkage. The extent of model loading was determined by gravimetric analysis and Zeisel methoxyl content. When reacted under simulated kraft pulping conditions, the polymer model,8-TrP, afforded moderate yields of guaiacol, a fragmentation product. The addition of 29% ofp-dioxane or DMSO drastically depressed the yield of guaiacol from8-TrP.The polymer bound dimer model8-TrPand monomer model6-TrPwere relatively unstable to the harsh, simulated pulping conditions. Some or all of the observed guaiacol fragmentation product could have come from degradation of polymer-released model.