Ethanol → 2-(1H-imidazol-1-yl)-1-phenylethanol

Participants

Reaction Steps

A solution of imidazole (47.0 g, 0.69 mol) in `super-dry` ethanol (175 ml) containing dry pyridine (3.0 ml) was stirred and heated to 75° when styrene oxide (80.0 g, 0.67 mol) was added dropwise at such a rate that the temperature of the reaction mixture was maintained at 80°-85°. Following the addition, the reaction mixture was stirred until the internal temperature had fallen to 50°. Isopropyl ether (300 ml) was then added to the reaction mixture, and the resulting mixture was poured into iced-water (1,000 ml). Separation of the resulting solid by filtration afforded the product which was washed with acetone (1×500 ml) and with ether (2×300 ml), to give 1-(2-hydroxy-2-phenylethyl)imidazole, m.p. 149°-151°.

Provenance & Evidence