Hydroxyamine hydrochloride → HCID 85700068, compound

Participants

Reaction Steps

To a stirred solution of 3′,4′-dimethoxy-2-propylvalerophenone (2.64 grams, 10 mmol) in a mixture of ethanol (45 milliliters) and water (10 milliliters) was added hydroxyamine hydrochloride (1.11 grams, 16 mmol) and sodium acetate (1.64 grams, 20 mmol) in water (10 milliliters). The solution was refluxed for 1 week. Reaction progress was monitored by TLC (30%, ethyl acetate/hexane, UV) and had reached an equilibrium after 1 week. The reaction was allowed to cool to ambient temperature and the ethanol was removed in vacuo to afford an oil/aqueous mixture which was extracted with methylene chloride, dried over magnesium sulfate and concentrated in vacuo to afford 2.93 grams of crude product as a yellow oil. The crude product was purified by flash chromatography (silica gel, 30%, ethyl acetate/hexane) to afford 1.28 grams (46%) of product as a yellow oil. 1H NMR (CDCl3) δ7.10-6.75(m, 3H), 3.78-3.96(m, 6H), 3.49-3.31(m, 0.5H), 2.65-2.50 (m, 0.5H), 1.91-1.19(m, 8H), 1.01-0.81(m, 6H). 13C NMR (CDCl3) δ162.5, 161.5, 149.5, 149.0, 148.6, 129.4, 125.9, 120.2, 111.2, 110.6, 110.5, 55.9, 55.8, 45.1, 38.9, 34.8, 21.3, 20.5, 14.2.

Provenance & Evidence