Hydrochloric Acid → 1-(1,4-Dimethoxynaphthalen-2-yl)-propane-1,2-dione 2-oxime

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Reaction Steps

The product from Step A (1.28 g, 5.24 mmol) was dissolved in ethyl ether (50 mL), anhydrous hydrogen chloride gas was added through this solution at moderate rate for 5 min. Butyl nitrite (0.68 mL, 5.77 mmol) was then added dropwise. Hydrogen chloride bubbling was continued for an additional 10 min. after addition of butyl nitrite was completed, the reaction mixture was then stirred at room temperature for 4 hr. The volatiles were removed by evaporation under vacuum and the residue was purified by flash chromatography (silica gel, ethyl acetate/hexane: 0.5/9.5) to give an oil (0.8 g): MS 274 (M+1).

Provenance & Evidence