Phenylacetaldehyde → Phenylacetaldoxime

Participants

Reaction Steps

Phenylacetaldehyde (12.0 g, 7.8 ml, 0.1 mol) was dissolved in EtOH (360 ml) and mixed while stirring successively with hydroxylamine hydrochloride (10.4 g, 0.15 mol) and abs. pyridine (9.7 ml, 0.12 mol). After stirring for 1.5 h at RT, the reaction mixture was concentrated, the residue taken up in toluene (1×100 ml) and the solvent removed again under vacuum. The oily residue was stirred with EtOAc (350 ml) and water (90 ml) for 15 min. Subsequently, the phases were separated. The organic phase was washed with water (2×80 ml), dried and concentrated. The oil obtained crystallised after a short time. The oil was recrystallised from n-hexane (20 ml). Compound V was obtained as a white solid in a yield of 31% (4.13 g) having a melting point of 90-94° C.

Provenance & Evidence