Reacción #417960

Ecuación de reacción

N-(3-Hydroxyphenyl)acetamide

butyryl chloride

→

title compound

Rendimiento 75.0%

3-acetamidophenyl butyrate

Rendimiento 75.0%

Disolventes

water

pyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITThe resulting crystalline suspension was left for 18 hrs
2. 2
   Otroethyl acetate (1:1, 1000 mL), the organic layer was separated
3. 3
   Lavadowashed with brine (3×1000 mL)
4. 4
   SecadoThe organic layer was dried over sodium sulfate
5. 5
   Concentraciónconcentrated in vacuo at 70° C.
6. 6
   Otroto remove pyridine
7. 7
   TemperaturaUpon cooling the oil
8. 8
   workup.ADDITIONThis solid was carefully added to a coarse 500 mL frit
9. 9
   Otrodried
10. 10
    LavadoMinimal washing with ice cold hexane
11. 11
    OtroThe final compound was collected

Procedimiento

N-(3-Hydroxyphenyl)acetamide (300 g) was stirred in pyridine (990 mL) followed by the addition of butyryl chloride (246 mL). This reaction was stirred at room temperature for 30 min. The resulting crystalline suspension was left for 18 hrs. to ensure completion. The mixture was dissolved in water and ethyl acetate (1:1, 1000 mL), the organic layer was separated and washed with brine (3×1000 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo at 70° C. to remove pyridine. Upon cooling the oil become a very low melting solid. This solid was carefully added to a coarse 500 mL frit and dried. Minimal washing with ice cold hexane was used to cake the solid. The final compound was collected to provide the title compound in 75% yield (440 g) as a light-yellow solid.

Fuente