The hydrodeoxygenation of benzyl alcohol, phenol, anisole, o-cresol, catechol, guaiacol, and vanillyl alcohol were carried out from 150 to 275 degrees C at 50 bar H-2 with a CuCr2O4 center dot CuO catalyst in a decalin solvent. The hydroxymethyl group of benzyl alcohol was found to be highly reactive towards hydrogenolysis to form toluene. Demethoxylation of anisole to form benzene was found to be the primary reaction pathway in contrast to demethylation and transalkylation reactions, which are more prevalent for conventional hydrotreating catalysts. The hydroxyl group of phenol strongly activated the aromatic ring towards hydrogenation forming cyclohexanol which was subsequently dehydrated and hydrogenated to form cyclohexane. Reaction networks of increasing complexity were devised for the major functional groups and integrated to describe the most complex molecule studied, vanillyl alcohol. (C) 2012 Elsevier B.V. All rights reserved.