Ethanol → α-(Difluoromethyl)-4-methylbenzenemethanol

Participants

Reaction Steps

A solution of 2.0 g (6.4 mmol) of 2,2-difluoro-1-(4-methylphenyl)-2-phenylsulfonylethanol and 1.9 mL (32 mmol) of absolute ethanol in 20 mL of dry tetrahydrofuran was treated with 0.74 g (32 mmol) of sodium spheres. After 90 minutes 1 mL of methanol followed by 1 mL of water were added to decompose unreacted sodium, and the mixture was poured into 100 mL of IN HCl. The resulting aqueous mixture was extracted with three 50 mL portions of dichloromethane. Combination, drying (MgSO4), and concentration of the organic layers afforded an orange liquid which was short path distilled to give 0.54 g (49% yield) of 2,2-difluoro-1-(4-methylphenyl)ethanol; bp 58° C. at 0.6 torr (lit 60°-62° C. at 0.5-0.6 torr; DePuy et al., J. Org. Chem., 1974, 39, 878); mass spectrum (70 eV) m/e (relative intensity) 172 (17, M +), 121 (100), 93 (68), 91 (75), 77 (64), 65 (25), 51 (46), 39 (24).

Provenance & Evidence