The oxidation of lignin model compounds was studied in conventional solvents in parallel with oxidations in ionic liquid solvents. Catalyst systems were investigated in ionic liquid solvents to determine how reaction rates and the selectivity for benzylic carbon oxidation were affected. Oxidation rates were often lower in ionic liquids than in conventional solvents ‒ as indicated by lower conversion in a standard reaction time ‒ likely due, at least in part, to the higher viscosity of ionic liquids. Mechano chemical treatment of Indulin AT kraft lignin by ball milling with KOH and toluene produced significant carbonyl functionality, among other changes. The chemical reactivity of the lignin was increased, resulting in greater lignin degradation from porphyrin oxidation followed by Baeyer-Villiger oxidation. The mechanochemical treatment produced a level of lignin oxidation that was similar to that produced by porphyrin-catalyzed oxidation. Combining mechanochemical treatment with porphyrin oxidation produced a synergistic positive effect on the depolymerization of lignin, as demonstrated by a significantly higher yield of monomers. The methyl ester of vanillic acid was obtained as the main monomeric product (after methylation), along with a small amount of methyl 5-carbomethoxyvanillate.