Benzenepropanal → 2-Hydroxy-4-phenylbutanenitrile

Participants

Reaction Steps

3-Phenylpropionaldehyde (0.40 mole) was added dropwise to a solution of sodium bisulfite (0.80 mole) in 240 mL water and 50 mL 95% ethanol at room temperature over a 30 min period. A solution of sodium cyanide (0.40 mole) in 60 mL water was added dropwise to the stirred white suspension over a 20 min period at room temperature. After continuing stirring for an additional 2 hrs, the reaction mixture was extracted with ether (4×250 mL). The extracts were combined, dried (MgSO4) and concentrated in vacuo to give 30.4 g (47%) of 2-hydroxy-4-phenylbutyronitrile as a viscous pale yellow oil.

Provenance & Evidence