Boron trifluoride etherate → p-Cyanobenzyl alcohol

Participants

Reaction Steps

Boron trifluoride diethyl etherate (0.85 mL, 6.8 mmol) was added to a solution of 4-cyanobenzoic acid (1.0 g, 6.8 mmol) and THF (10 mL). At room temperature, borane-tetrahydrofuran complex (1.0 M, 13.6 mL) was added to the reaction mixture drop-wise with no observed exotherm. The reaction mixture was stirred at room temperature for 2 hours and concentrated in vacuo. The resulting residue was taken up in ethyl acetate (50 mL), washed with saturated NaHCO3 and brine, dried (Na2SO4), filtered and concentrated in vacuo to give the title compound (0.900 g, 95% yield) as a solid.

Provenance & Evidence