Ethanol → α-(Difluoromethyl)-4-methylbenzenemethanol

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).

1. additionwere added
2. extractionThe resulting aqueous mixture was extracted with three 50 mL portions of dichloromethane
3. dry with materialCombination, drying (MgSO4), and concentration of the organic layers
4. customafforded an orange liquid which
5. distillationdistilled

ORD record

ord-b36465d08bf847769772b94db8857c28

Source dataset

uspto-grants-1991_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04999429