Hydroxyamine hydrochloride → 4-Methyl-3-phenyl-4-pentenenitrile

Participants

Reaction Steps

4-Methyl-3-phenyl-4-pentenal (15.27 g; 0.077 mol) and hydroxylamine hydrochloride (8.1 g; 0.116 mol) were heated together in 95% ethyl alcohol (125 ml) at reflux under nitrogen for 3 hours. Ethyl alcohol was removed on the rotavapor and the residue partitioned between n-heptane and water (100 ml each). The aqueous phase was reextracted with n-heptane (100 ml). Each organic phase was washed with 5% aqueous HCl, water, aqueous saturated NaHCO3 and brine (100 ml each). Combined extracts were dried over anhydrous sodium sulfate. The product was purified by column chromatography on silica gel (eluting with heptane/ethyl acetate 10:1 to 5:1) followed by bulb-to-bulb distillation. 4.9 g of the desired product were obtained (0.0285 mol; yield=37%).

Provenance & Evidence