Hydroxyamine hydrochloride → 1-(2-Chlorophenoxy)-2-propanone oxime

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Reaction Steps

1-(2-Chlorophenoxy)acetone (106.6 g, 0.58 mol) (J. Am. Chem. Soc., 75, 1953, 1134) was added to a solution of hydroxylamine hydrochloride (27.8 g, 4 mol) in 2N sodium hydroxide solution (420 ml) and sufficient ethanol to give a clear solution. The reaction mixture was refluxed for 30 minutes then concentrated in vacuo, the crude residue was extracted with diethyl ether (3×200 ml). The combined organic layers were dried over magnesium sulphate and concentrated in vacuo. The residue was distilled to give the title product (134-136° C./1.35 mmHg) (4.5 g, 3.9%); 1H NMR (CDCl3 400 MHz) δ: 2.05 (s, 3H), 5.00 (s, 2H), 6.90-7.00 (m, 2H), 7.10 (t, 1H), 7.30 (d, 1H), 7.60 (s, 1H). Anal. Found C, 54.95; H, 5.05. C9H10NO2Cl requires C, 54.15; H, 5.05%.

Provenance & Evidence