Piperonal → (Benzodioxol-5-yl)(3,5-dimethoxyphenyl)methanol

Participants

Reaction Steps

1-Bromo-3,5-dimethoxybenzene (0.47 g, 3.14 mmol), benzo[1,3]dioxole-5-carbaldehyde (0.75 g, 3.46 mmol), and n-butyl lithium (1.38 ml, 3.46 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 was purified via flash column chromatography (5% EtOAc in hexane gradient to 30% EtOAc in hexane in about 40 min.) to give Benzo[1,3]dioxol-5-yl-(3,5-dimethoxy-phenyl)-methanol as an off-white oil (0.73 g, 81%): 1HNMR (CDCl3) 6.87-6.83 (m, 2H, Ar), 6.77-6.74 (m, 1H, Ar), 6.53 (d, J=2 Hz, 2H, Ar), 6.36 (t, J=2 Hz, 1H), 5.93 (m, 2H, CH2), 5.68 (d, J=3 Hz, 1H, CHOH), 3.77 (s, 6H, 2OCH3), 2.15 (d, J=3 Hz, 1H, OH). The product was carried over to the next step.

Provenance & Evidence