Water → Benzaldehyde, 5-chloro-2-hydroxy-, oxime

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Reaction Steps

Pyridine (20 ml) was added to a stirred suspension of 5-chloro-2-hydroxybenzaldehyde (5.0 g) and hydroxylamine hydrochloride (2.77 g) in ethanol (20 ml) and stirring was continued for 18 hours. The mixture was then added to water (150 ml) and extracted with ether (3×50 ml). The combined extracts were washed with water (2×50 ml), dried (MgSO4) and concentrated to give a yellow oil which slowly crystallised on standing. The solid was collected by filtration and washed with hexane to give 5-chloro-2-hydroxybenzaldoxime (4.25 g) as white crystals, m.p. 125°-126° C.; NMR: 6.91(1H,d,J=5 Hz), 7.15(1H,d,J=2.5Hz), 7.22(1H,dd,J=8,2.5Hz); 7.55(1H,b), 8.16(1H,s), 9.26(1H,b).

Provenance & Evidence