Ethanol → 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 (100 mg, 0.49 mmol), anhydrous ethanol (5 ml), triethylamine (102 ml) and hydroxylamine hydrochloride (51 mg, 0.73 mmol). The reaction mixture was heated under reflux for 3 hr, then evaporated in vacuo. The resulting solid was purified by flash column chromatography, (SiO2, ethyl acetate/petroleum ether, 35:65, v/v), furnishing the title compound as short white needles (107 mg, 100%). δH(CD3OD) 1.44-1.61 (2H, m), 1.81-1.88 (1H, m), 1.94-2.00 (2H, m), 2.19-2.27 (1H, m), 2.43 (1H, d), 3.04-3.10 (1H, m), 3.38 (1H, m), 6.22-6.25 (1H, m), 6.28 (1H, d), 6.84-6.86 (1H, m); m/z (EI−) 220.

Provenance & Evidence