Ammonium Chloride → alpha-Methyl-4-(trifluoromethoxy)benzenemethanol

Participants

Reaction Steps

A cooled (0° C.) solution of 4-(trifluoromethoxy)benzaldehyde (3.000 g; 15.78 mmol) in anh. THF (50 ml) was treated dropwise with a solution of methylmagnesium bromide (3 M in Et2O; 6.30 ml; 18.90 mmol), and the resulting mixture was stirred at rt, under nitrogen, for 4 h. The resulting reaction mixture was cooled to 0° C., and aq. sat. NH4Cl (30 ml) was added dropwise. The separated aq. layer was further extracted with AcOEt (3×20 ml), and the mixed organic layers were dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=40/1) afforded 1-(4-(trifluoromethoxy)phenyl)ethanol as a colorless oil. LC-MS (conditions D): tR=0.88 min.; no ionisation.

Provenance & Evidence