Although lignin is the most abundant natural phenolic polymer, its phenol activity is extremely low. Because most phenolic hydroxyl groups of lignin precursors were etherified in the biosynthetic process. In the present work, successive cleavage of ether linkages of lignin was carried out. The first step is the phase-separation process composed of phenols and concentrated acid. In the process, native lignin was modified by phenol derivatives to selectively grafted benzyl position, the most reactive sites, to give1,1-Bis(aryl) propane type lignin-based recyclable polymer (lignophenol) that has the original interunit linkage of lignin and have high phenolic content. The second step is cleavage of C beta aryl ether linkages by switching functions of lignophenol under the mild alkaline condition. The reaction mechanism was confirmed that with C alpha phenolic nuclei (switching devise) having an OH ortho to the linking position with lignin, the phenoxy anions readily nucleophilically attack C beta, so that C beta aryl ether linkages were cleaved. The third step is demethylation of the aromatic methoxyl groups. Demethylation of methoxyl group in lignophenol depolymerized products was carried out using boron tribromide. The methoxyl group of guaiacyl aryl coumaran was effectively demethylated to give catechol type aryl coumaran dimmer.