The reactions of two sets of lignin model compounds over a sulfided CoOMoO3/γ-Al2O3 catalyst were studied. The first set mimicked lignin methoxyphenol residues and comprised 4-methyl-guaiacol, 4-methyl catechol, eugenol and vanillin. Deoxygenation and hydrogenation were facile and led to ultimate molar yields of single-ring products as high as 0.70. The selectivity to single-ring products increased with increases in temperature, o-hydroxydiphenylmethane, phenyl ether and o,o’-biphenol constituted the second set that mimicked thermally stable lignin bonds.Fragmentation of o-hydroxydiphenylmethane and phenyl ether occurred readily; o,o’-biphenol reacted to dibenzofuran.