Benzyl Bromide → 4-Benzyloxy-2-(trifluoromethyl)benzayl alcohol

Participants

Reaction Steps

To a solution of 4-(hydroxymethyl)-3-(trifluoromethyl)phenol (for a preparation see Intermediate 17)(3.86 g, 20.1 mmol) in ethanol (80 mL) was added benzyl bromide (2.4 ml, 20.2 mmol, Aldrich) and then 2 M sodium hydroxide (11 ml, 22 mmol). The mixture was stirred at ambient temperature overnight under nitrogen. The solvent was removed in vacuo to leave an aqueous suspension. The residue was partitioned between dichloromethane (100 ml) and water (100 ml). The phases were separated and the aqueous phase extracted with dichloromethane (50 ml). The combined organic extracts were dried (MgSO4), filtered and the solvent removed in vacuo to leave an oil. The residue was loaded in dichloromethane and purified on silica 100 g using 0-100% ethyl acetate-cyclohexane. The appropriate fractions were combined and evaporated in vacuo to give the title compound as a white solid (4.68 g);

Provenance & Evidence