The significance of condensation reactions at the 5-position of the aromatic ring of lignin to the overall pulping process has been evaluated using lignin model compounds. Reactions of 5-hydroxymethylcreosol, as a model for 5-substituted lignins formed when formaldehyde is released during pulping, have shown that such groups will react viaortho-quinonemethides to give alkali-stable carbon-carbon bonded condensation products. The amount of condensation depends on the type of pulping liquor used, with less formed in the kraft and soda-anthraquinone (AQ) processes than in the soda process. In these liquors the hydrosulphide or anthrahydroquinone (AHQ) ions present can compete effectively with phenoxide ion for the reactiveo-quinonemethide intermediate.