反応 #417960

反応方程式

N-(3-Hydroxyphenyl)acetamide

butyryl chloride

→

title compound

収率 75.0%

3-acetamidophenyl butyrate

収率 75.0%

溶媒

water

pyridine

反応条件

後処理

1. 1
   workup.WAITThe resulting crystalline suspension was left for 18 hrs
2. 2
   その他ethyl acetate (1:1, 1000 mL), the organic layer was separated
3. 3
   洗浄washed with brine (3×1000 mL)
4. 4
   乾燥The organic layer was dried over sodium sulfate
5. 5
   濃縮concentrated in vacuo at 70° C.
6. 6
   その他to remove pyridine
7. 7
   温度Upon cooling the oil
8. 8
   workup.ADDITIONThis solid was carefully added to a coarse 500 mL frit
9. 9
   その他dried
10. 10
    洗浄Minimal washing with ice cold hexane
11. 11
    その他The final compound was collected

実験手順

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.

出典