Reacción #62815

Ecuación de reacción

2-(p-nitrophenyl)-propionic acid

thionyl chloride

→

1-methyl-cyclohexyl 2-(p-nitrophenyl)-propionate

Rendimiento 48.0%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato cool
2. 2
   Otrothe solvent was evaporated under reduced pressure
3. 3
   workup.DISSOLUTIONThe residual oil was dissolved in 400 ml of dry toluene
4. 4
   workup.ADDITION100 g of 1-methylcyclohexanol were added to the solution
5. 5
   TemperaturaThe stirred mixture was heated at 80° C. for 1 hour
6. 6
   Otroat ambient temperature
7. 7
   Otroovernight
8. 8
   LavadoThe solution was washed with 5% NaHCO3 solution
9. 9
   Secadowater, dried over MgSO4
10. 10
    Otrofinally evaporated to dryness
11. 11
    OtroThe crude mixture was purified over a column of 600 g of silica

Procedimiento

A stirred mixture of 97.5 g of 2-(p-nitrophenyl)-propionic acid [J. Med. Chem. Vol. 26, pages 222-226 (1983)], 40 ml of thionyl chloride and 500 ml of dry toluene was heated at 80° C. for 5 hours. The mixture was then allowed to cool and the solvent was evaporated under reduced pressure. The residual oil was dissolved in 400 ml of dry toluene, and 100 g of 1-methylcyclohexanol were added to the solution. The stirred mixture was heated at 80° C. for 1 hour and then at ambient temperature overnight. The solution was washed with 5% NaHCO3 solution, then water, dried over MgSO4 and finally evaporated to dryness. The crude mixture was purified over a column of 600 g of silica using CHCl3 as the eluant 34.95 g (24% yield) of 1-methyl-cyclohexyl 2-(p-nitrophenyl)-propionate as a golden yellow liquid.

Fuente