Diethyl Ether → 1-Phenylnaphthalen-2-ol

Participants

Reaction Steps

To solution of 2-methoxy-1-phenylnaphthalene (13.0 g, 55.5 mmol) in methylene chloride (300 mL), added dropwise was solution of boron tribromide (670 mL) (1M in methylene chloride) at −78° C., and the mixture reacted for three hours while slowly raising the temperature to ambient temperature. Then, mixture of ice (150 g) and diethyl ether (250 mL) was added thereto. The organic layer was isolated, and the aqueous layer was extracted with diethyl ether. The combined organic layer was dried over magnesium sulfate and evaporated to remove the volatile substances. Purification via silica gel column chromatography (eluent: mixture of hexane and methylene chloride) gave 1-phenylnaphthalen-2-ol (10.0 g, yield: 81.8%) as white solid.

Provenance & Evidence