Benzaldehyde → (Z)-Benzaldehyde oxime

Participants

Reaction Steps

Benzaldehyde (5.31 g, 50.0 mmol) was dissolved in ethanol (60 ml)-water (30 ml), and hydroxylamine hydrochloride (5.21 g, 1.5 Eq) and anhydrous sodium carbonate (Na2CO3, 3.97 g, 0.75 Eq) were added thereto at 0° C. When a large amount of solid was formed after about one minute, water-ethanol (1:1, 60 ml) was added, and the mixture was stirred for one hour. Saturated aqueous sodium chloride solution (100 ml) was added, and the mixture was extracted twice with ethyl acetate (300 ml). The extract was washed with 1.0 N aqueous sodium bicarbonate solution (NaHCO3, 100 ml×2), dried (anhydrous Na2SO4), and concentrated under reduced pressure to give the title compound (6.06 g, Yield 99%) as a white powder as a mixture of cis and trans.

Provenance & Evidence