Sodium Acetate → O-Methyl-4-(2,4-dihydroxyphenyl)cyclohexanone Oxime

Participants

Reaction Steps

To a round bottomed flask, equipped with magnetic stirrer was added 4-(2,4-dihydroxyphenyl)cyclohexanone (21 mg, 0.10 mmol), anhydrous ethanol (3 ml), sodium acetate (16 mg, 0.20 mmol) and O-methylhydroxylamine hydrochloride (9 mg, 0.22 mmol). The reaction mixture was heated under reflux for 6 hr, then partitioned between ethyl acetate (10 ml) and water (10 ml). The organic layer was dried over anhydrous calcium sulphate, filtered and evaporated in vacuo furnishing a colourless oil. Purification via flash column chromatography (SiO2, ethyl acetate/petroleum ether, 1:1, v/v), afforded the title compound as a white solid (11 mg, 47%). δH (CD3OD) 1.43-1.63 (2H, m), 1.81-1.92 (2H, m), 1.93-2.20 (2H, m), 2.24 (1H, dt), 2.38-2.44 (1H, m), 3.07 (1H, tt), 3.78 (3H, s), 6.20-6.23 (1H, m), 6.26 (1H, d), 6.85 (1H, d); m/z (ES−) 234.

Provenance & Evidence