This experiment was carried out to contribute to the synthetic methods of ligin model compounds. The ligin model compounds of arylglycerol-${eta}$-arylether structure were synthesized in high yield through three or four reaction steps. The starting compound was commercial 3, 4, 5-trimethoxyace tophenone and the final compounds were 1-(2-methoxyphenoxy)-2 - (3, 4, 5 - trimethoxyphenyl)-ethanol(IV), 1-(3, 4, 5-trimethoxyphenyl)-2-(2-methoxy-phenoxy)-propandiol-1,3 (VI), 1-(2, 6-dimethoxyphenoxy)-2-(3, 4, 5-trimethoxyphenyl)-ethanol (VIII), and 1-(3, 4, 5-trimethoxyphenyl)-2-(2, 6-dimethoxyphenoxy)-propandiol-1, 3 (X). The structures of synthetic compounds were identified by IR, $^1H$-NMR spectroscopy and Mass spectrometry.