Reacción #1747829

Ecuación de reacción

NaOH

n-propylamine

3-(4-methoxyphenyl)-propionic acid

thionylchloride

→

amide

3-(4-methoxyphenyl)-propionic acid n-propylamide

Disolventes

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe volatiles were evaporated
2. 2
   workup.DISSOLUTIONthe resulting oil was dissolved in dichloromethane (100 mL)
3. 3
   Otrowere separated
4. 4
   Extracciónthe aqueous layer was extracted with dichloromethane (3×50 mL)
5. 5
   LavadoThe combined organic layers were washed with water (50 mL) and brine (50 mL)
6. 6
   Secadowas dried over MgSO4
7. 7
   OtroEvaporation of the solvent

Procedimiento

3-(4-methoxyphenyl)-propionic acid (8.8 g, 49 mmol) was refluxed in dichloromethane (200 mL) with thionylchloride (6.6 mL, 90 mmol) for 1 h. The volatiles were evaporated and the resulting oil was dissolved in dichloromethane (100 mL). This was added to a vigorously stirred mixture of 5% aqueous NaOH (200 mL), dichloromethane (100 mL) and n-propylamine (3.0 mL, 71 mmol). After stirring for 1 h the layers were separated and the aqueous layer was extracted with dichloromethane (3×50 mL). The combined organic layers were washed with water (50 mL) and brine (50 mL) and was dried over MgSO4. Evaporation of the solvent gave the amide in quantitative yield (10.7 g, 49 mmol, 100%). IR (neat) cm−1 3300, 2961; 1734, 1642; MS (EI) m/z 221 (M+) Analyses were in agreement with literature data.

Fuente