Hydrochloric Acid → 2-(Hydroxyimino)-1-phenylbutan-1-one

Participants

Reaction Steps

To a stirred solution of the butyrophenone (300 mg, 2.0 mmol) in tetrahydrofuran (8 mL) was added t-butyl nitrite (0.475 mL, 4.0 mmol) and hydrochloric acid (4N in dioxane, 0.65 mL, 2.6 mmol). The reaction was stirred at RT for 3 hours, then the solvent was evaporated and the residue was purified by Prep HPLC (ammonium acetate/water/acetonitrile) to give the title material (0.200 g, 56%). HPLC 91% (220 nm), LCMS (+ESI, M+H+) m/z 178; 1H NMR (400 MHz, methanol-d4) δ (ppm): 1.13 (3H, t, J=7.6 Hz), 2.71 (2H, qa, J=7.6 Hz), 7.45 (2H, br t), 7.57 (1H, br t), 7.90 (2H, d, J=7.0 Hz).

Provenance & Evidence