反应详情

温度

5 °C

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).

1. extractionextracted with ethyl acetate (4×100 mL)
2. washThe combined extracts were washed with aqueous sodium chloride solution (50 mL)
3. dry with materialdried over sodium sulfate
4. filtrationfiltration and removal of solvent under vacuum the product, 4-(hydroxymethyl)benzonitrile
5. custom(9.44 g; 93%) was obtained as a white solid