반응 #417960

반응 방정식

N-(3-Hydroxyphenyl)acetamide

butyryl chloride

→

title compound

수율 75.0%

3-acetamidophenyl butyrate

수율 75.0%

용매

water

pyridine

반응 조건

후처리

1. 1
   workup.WAITThe resulting crystalline suspension was left for 18 hrs
2. 2
   기타ethyl acetate (1:1, 1000 mL), the organic layer was separated
3. 3
   세척washed with brine (3×1000 mL)
4. 4
   건조The organic layer was dried over sodium sulfate
5. 5
   농축concentrated in vacuo at 70° C.
6. 6
   기타to remove pyridine
7. 7
   온도Upon cooling the oil
8. 8
   workup.ADDITIONThis solid was carefully added to a coarse 500 mL frit
9. 9
   기타dried
10. 10
    세척Minimal washing with ice cold hexane
11. 11
    기타The final compound was collected

실험 절차

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.

출처