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

Participants

Reaction Conditions

Reaction Steps

3,5-Dimethoxybenzaldehyde (5.0 g, 30 mmol) was dissolved in 150 mL THF in a 500 mL round bottom flask. 3,5-Dimethoxyphenyl magnesium chloride (1 M in THF, 45 mL) was added slowly. The reaction was heated at 40° C. for 4 hours then quenched with saturated ammonium chloride. The mixture was extracted with 3 portions of ether and the combined organic layers washed with brine, dried over anhydrous MgSO4, then concentrated to a crude pale yellow solid which was carried forward to the next step: 1H NMR (250 MHz, C6D6): δ 3.29 (d, J=5.0 Hz, 12H), 6.46 (m, 2H), 6.56 (m, 1H), 6.76 (m, 2H), 7.04 (t, J=8.2 Hz, 1H).

Provenance & Evidence