Potassium Carbonate → HCID 22000662, compound

Participants

Reaction Steps

3-(3,5-Dimethoxybenzyloxy)-benzene-1,2-diol (0.28 g, 1.03 mmol), 4-bromomethyl-1,2-dimethoxy-benzene (0.24 g, 1.03 mmol), potassium carbonate (0.14 g, 1.03 mmol) and 18-crown-6-ether (0.03 g, 0.11 mmol) were stirred together at room temperature in acetone (30 cm3, 99%) under nitrogen for 21 hours. The solution was evaporated under reduced pressure, and the residue was taken up in dichloromethane (10 cm3) and water (10 cm3). The aqueous layer was extracted with dichloromethane (2×10 cm3), and the combined extracts were washed with water (2×40 cm3), dried (MgSO4), and evaporated under reduced pressure. The residue was taken up in diethyl ether (30 cm3) and washed with sodium hydroxide (2×15 cm3, 3% aqueous solution). The sodium hydroxide portion was saturated with solid carbon dioxide pellets and extracted with diethyl ether (3×30 cm3). The extracts were evaporated under reduced pressure to give a crude oil. The oil was chromatographed (SiO2, heptane:ethyl acetate, 1:1) to give the phenol, (0.14 g, 31%) as a clear oil.

Provenance & Evidence