Hydroxyamine hydrochloride → HCID 85521050, compound

Participants

Reaction Steps

To a stirred solution of 3′,4′-dimethoxyvalerophenone (0.08 grams, 3.60 mmol) in a mixture of ethanol (25 milliliters) and water (5 milliliters) was added hydroxyamine hydrochloride (0.40 grams, 5.76 mmol) and sodium acetate (0.59 grams, 7.20 mmol) in water (5 milliliters). The solution was refluxed for two days. Reaction progress was monitored by TLC (20%, ethyl acetate/hexane, UV) and was complete after 2 days. The reaction was allowed to cool to ambient temperature and the ethanol was removed in vacuo to afford an oil/aqueous mixture. The mixture was extracted with methylene chloride. The dried extracts were concentrated in vacuo to afford 0.93 grams of crude product as a yellow oil. The crude product was purified by flash chromatography (silica gel, 20%, ethyl acetate/hexane) to afford 0.56 grams of product as a yellow oil: 1H NMR (CDCl3) δ8.23-8.01(br s, 1H), 7.30-7.05(m, 2H), 6.93-6.81(m, 1H), 3.91(s, 3H), 3.90(s, 3H), 2.84-2.70(m, 2H), 1.74-1.31(m, 4H), 0.93(t, J=7.2 Hz, 3H);13 C NMR (CDCl3) δ159.6, 150.1, 148.9, 128.5, 119.3, 110.6, 108.9, 55.9, 28.7, 25.6, 22.9, 13.8.

Provenance & Evidence