2-Nitrobenzaldehyde → Ethyl 3-(2-nitrophenyl)propanoate

Participants

Reaction Steps

A solution of 2-nitrobenzaldehyde (132 mmol; 20.0 g) in absolute ethanol (220 ml) was added to a mixture of triethylphosphonium acetate (159 mmol; 35.7 g; 31.9 ml) and anhydrous potassium carbonate (397 mmol; 54.9 g). The mixture was refluxed with vigorous stirring for 1 hour 30 minutes. After cooling, the ethanol was removed under reduced pressure, water (500 ml) was added and the resulting solution was extracted with ethyl acetate (3×300 ml). The combined organic phases were washed with saturated NaCl solution (3×300 ml), dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude product obtained was purified on a column of alumina (eluting with chloroform) to give 27.6 g (94%) of final product:

Provenance & Evidence