Benzyl Alcohol → 4-(Benzyloxy)-3-(trifluoromethyl)benzoic acid

Participants

Reaction Steps

To a solution of potassium t-butoxide (27.5 g) in N,N-dimethylformamide (120 ml) was added dropwise a solution of benzyl alcohol (15.9 ml) in N,N-dimethylformamide (60 ml) over min. The mixture was stirred for 30 min, and a solution of 4-fluoro-3-trifluoromethylbenzoic acid (20.0 g) in N,N-dimethylformamide (90 ml) was added under ice-cooling. The mixture was stirred at room temperature for 1 hr, and further at 50° C. for 1 hr. The reaction mixture was added to ice water, and acidified with 1M hydrochloric acid (300 ml). The precipitated solid was collected by filtration, and washed with water and then hexane to give the object product (28.2 g) as a white powder.

Provenance & Evidence