Potassium Carbonate → 2-(2-Dimethylaminoethoxy)-4-nitroanisole

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Reaction Steps

A stirred solution of 2-methoxy-5-nitrophenol (5.0 g, 0.029 mole) and potassium carbonate (8.3 g, 0.060 mole) in acetone (200 ml) and water (60 ml) was treated with N,N-dimethylaminoethyl chloride hydrochloride (8.64 g, 0.060 mole) and heated under reflux for 10 h. The mixture was concentrated under vacuum to approx. 80 ml volume, then acidified with 2M HCl acid (150 ml) and washed with ethyl acetate (2×80 ml). The acid solution was basified with K2CO3 and extracted with ethyl acetate (2×100 ml). The combined extract was dried (Na2 SO4) and concentrated under vacuum to afford the title compound as a yellow solid (4.87 g, 70%).

Provenance & Evidence