Sodium Hydroxide → Ethanone, 1-(1,3-benzodioxol-5-yl)-, oxime

Participants

Reaction Conditions

Reaction Steps

Powdered sodium hydroxide (6.6 g, 170 mmol, 9.0 equiv) and hydroxylamine hydrochloride (3.8 g, 55 mmol, 3.0 equiv) were sequentially added to a stirred suspension of and 3,4-(methylenedioxy)acetophenone (9) (3.0 g, 18 mmol, 1.0 equiv) in ethanol (32 mL) and distilled water (13 mL) at 25° C. The reaction vessel was equipped with a reflux condenser and heated to 80° C. via oil bath for 3 h. The reaction mixture was cooled to 25° C., diluted with saturated aqueous ammonium chloride (400 mL), and the product was extracted with dichloromethane (5×125 mL). The combined organic layers were dried (sodium sulfate), gravity filtered, and concentrated by rotary evaporation. The residue was purified by rinsing with cold dichloromethane followed by vacuum filtration to afford 12 (2.9 g, 87% yield) as an off-white crystalline solid. Rf=0.41 (25% ethyl acetate in hexane); 1H NMR (500 MHz, CDCl3) δ 7.77 (s, 1H, OH), 7.18 (d, 1H, J=1.5 Hz, ArH), 7.10 (dd, 1H, J=6, 1.5 Hz, ArH), 6.81 (d, 1H, J=6 Hz, ArH), 5.99 (s, 2H, OCH2O), 2.24 (s, 3H, CH3); IR (neat film) 3296 (w, br), 3228 (w, br), 2907 (w), 1505 (s), 1266 (s), 1227 (s), 1037 (s) cm−1; HRMS (EI) m/z: Calcd for C9H9NO3 (M+) 179.0582, observed 179.0584.

Provenance & Evidence