Syringylalcohol (1), α-methyl syringylalcohol (2), 3, 4, 5-trime-thoxyphenyl methylcarbinol (3) were dispersed onto filter paper pulp or linter pulp, and treated, respectively, with a ceramic ball mill (CBM) or a vibration ball mill (VBM-1 or -2) under air for 1h. Mechanical treatment of VBM-2, having the more rigid surface of linter pulp, furnished thep-carbonylphenols (5), (6), and 3, 5-dimethoxy-p-benzoquinone (7). Mechanical treatments of syringylgl-ycerol-β-guaiacyl ether (4) with CBM, VBM, and a laboratory refiner provided α-(2-methoxyphenoxy)-β-hydroxypropiosyringone (8) in the highest yield and a less yield ofp-quinone derivative (7) and others as shown in TABLE 2 and FIGURE 3. When treated the resultant mixture with alkaline H202, the chromophore (III) can be decomposed, but remarkable amounts of the leucochromophre (IV) are produced as shown in FIGURE 4.