3,5-Dimethoxybenzaldehyde → Bis(3,5-dimethoxyphenyl)methanol

Participants

Reaction Steps

3,5-Dimethoxybenzaldehyde (0.84 g, 5.03 mmol), 1-bromo-3,5-dimethoxybenzene (1.20 g, 5.53 mmol), and n-butyl lithium (2.20 ml, 5.53 mmol) were treated in the same manner as described above for the synthesis of (2,3-dihydrobenzo [1,4]dioxin-6-yl)-(3,5-dimethoxyphenyl)methanol. The crude material was purified via flash column chromatography (10% EtOAc in hexane gradient to 60% EtOAc in hexane in about 40 min.) to give Bis-(3,5-dimethoxy-phenyl)-methanol as an off-white solid (1.31 g, 86%): 1HNMR (CDCl3) 6.55 (d, J=2 Hz, 4H, Ar), 6.36 (t, J=2 Hz, 2H, Ar), 5.67 (d, J=3 Hz, 1H, CHOH), 3.77 (s, 12H, 4OCH3), 2.24 (d, J=3 Hz, 1H, OH). The product was carried over to the next step.

Provenance & Evidence