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

Reaktionsgleichung

[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O)([O-:3])=[O:2].[C:12]([O-:15])(=[O:14])[CH3:13].[CH2:16]([PH+](CC)CC)[CH3:17].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][CH2:13][C:12]([O:15][CH2:16][CH3:17])=[O:14])([O-:3])=[O:2]

Komponenten

Versuchsvorschrift

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: