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

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:

1. temperatureThe mixture was refluxed
2. temperatureAfter cooling
3. customthe ethanol was removed under reduced pressure, water (500 ml)
4. additionwas added
5. extractionthe resulting solution was extracted with ethyl acetate (3×300 ml)
6. washThe combined organic phases were washed with saturated NaCl solution (3×300 ml)
7. dry with materialdried over anhydrous sodium sulfate
8. customevaporated under reduced pressure
9. customThe crude product obtained
10. customwas purified on a column of alumina (eluting with chloroform)

ORD record

ord-9e4fc082d3c74deeadb2c061afa04a77

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08686147B2