Water → p-Cyanobenzyl alcohol

Participants

Reaction Conditions

Reaction Steps

A stirred suspension of 4-formylbenzonitrile (10.0 g; 0.0763 moles) in methanol (100 mL) under nitrogen was cooled to 5° C. Sodium borohydride (1.45 g; 0.0382 moles) was added. After 30 minutes the mixture was added to water (300 mL) and extracted with ethyl acetate (4×100 mL). The combined extracts were washed with aqueous sodium chloride solution (50 mL) and dried over sodium sulfate. Following filtration and removal of solvent under vacuum the product, 4-(hydroxymethyl)benzonitrile, (9.44 g; 93%) was obtained as a white solid. 1H NMR (400 MHz) CDCl3 δ 7.61-7.66 (2H, m), 7.45-7.50 (2H, m), 4.78 (2H, d, J=5.5 Hz), 2.27 (1H, t, J=5.5 Hz).

Provenance & Evidence