Acetic Acid → 2-[(3,5-Dimethoxyphenyl)methoxy]phenol

Participants

Reaction Steps

A solution of potassium hydroxide (1.75 g, 31.26 mmol) in ethanol (30 cm3, absolute) and water (30 cm3) was added in portions 15 minutes apart to 1-[3,5-dimethoxy-benzyloxy]-2-[toluene-4-sulfonyloxy]benzene (0.68 g, 1.64 mmol). After heating to reflux for 1 hour, the cooled solution was neutralized with glacial acetic acid and evaporated under reduced pressure. The residue was extracted with diethyl ether (3×20 cm3), and the extracts were washed with sodium bicarbonate (40 cm3) and sodium hydroxide (3×20 cm3, 3% aqueous solution). The sodium hydroxide portion was saturated with solid carbon dioxide pellets, and the precipitate was removed by filtration to give the phenol (0.32 g, 74%).

Provenance & Evidence