In this study, we carried out successive cleavage of three type ether linkages of lignin through the reverse pathway of lignin biosynthetic mechanism. The first step is cleavage of benzyl aryl ether and conversion to lignophenol through the phase-separation system. The second step is cleavage of C-beta aryl ether linkages by switching functions of lignophenol utilized neighboring group participation reaction under the mild alkaline condition. The third step is demethylation of the aromatic methoxyl groups and conversion to monophenols by Lewis acid treatment. Conversions to monophenols of depolymerized lignophenol were carried out using boron trifluoride. The guaiacol and p-cresol were recovered from depolymerized lignophenol quantitatively Trough these cleavage of ether linkages and conversion to monophenols of lignin, we carried out activation and depolymerization of lignin for chemical feedstocks.