Ethyl Acetate → (4-(4-(Trifluoromethoxy)benzyl)phenyl)methanol

Participants

Reaction Steps

LiAlH4 (55 mg, 1.45 mmol) was added to a solution of ester 94 (203 mg, 0.65 mmol) in ether (5 mL) and the mixture was stirred at room temperature for 3 h, then EtOAc (150 mL) was added. The organic layer was washed with water, the aqueous layer was re-extracted with EtOAc (100 mL), and the combined organic layers were washed with brine, dried (Na2SO4) and concentrated under reduced pressure to give {4-[4-(trifluoromethoxy)benzyl]phenyl}methanol (95) (185 mg, quant.) as a white solid: mp (EtOAc/hexane) 60-61° C.; 1H NMR (CDCl3) δ 7.32-7.27 (m, 2H), 7.20-7.14 (m, 4H), 7.13-7.09 (m, 2H), 4.67 (s, 2H), 3.98 (s, 2H); HREIMS calcd for C15H13F3O2 m/z (M+) 282.0868, found 282.0866.

Provenance & Evidence