反应详情

温度

110 °C

To a solution of 1.902 q (12.68 mmol) of 3-carboxybenzaldehyde in 10 mL of glacial acetic acid, was added 2.848 mL (2.970 g, 38.04mmol) of nitroethane and 1.080 g (13.95 mmol) of ammonium acetate. The solution was then heated with stirring under nitrogen in a 110° C. oil bath. Then, all of the solid went into solution near 60° C. and the mixture turned a deep yellow color. After 3 hours, thin layer chromatography with 3:1 hexane/EtOAc indicated that no starting material remained. The reaction mixture was cooled to room temperature, and then partitioned between water and methylene chloride, with acidification to about pH2 with 6 M HCl. The organic layer was washed with 6 M HCl, then dried with magnesium sulfate. The solvents were then removed with a rotary evaporator, yielding 2.768 g (98%) of crude material, which was carried on without further purification because of the difficulty of chromatographing the very polar carboxylic acid.

1. temperatureThe solution was then heated
2. customwent into solution near 60° C.
3. temperatureThe reaction mixture was cooled to room temperature
4. custompartitioned between water and methylene chloride, with acidification to about pH2 with 6 M HCl
5. washThe organic layer was washed with 6 M HCl
6. dry with materialdried with magnesium sulfate
7. customThe solvents were then removed with a rotary evaporator