تفاعل #417960

معادلة التفاعل

N-(3-Hydroxyphenyl)acetamide

butyryl chloride

→

title compound

المردود 75.0%

3-acetamidophenyl butyrate

المردود 75.0%

المذيبات

water

pyridine

ظروف التفاعل

المعالجة

1. 1
   workup.WAITThe resulting crystalline suspension was left for 18 hrs
2. 2
   أخرىethyl acetate (1:1, 1000 mL), the organic layer was separated
3. 3
   غسيلwashed with brine (3×1000 mL)
4. 4
   تجفيفThe organic layer was dried over sodium sulfate
5. 5
   تركيزconcentrated in vacuo at 70° C.
6. 6
   أخرىto remove pyridine
7. 7
   درجة الحرارةUpon cooling the oil
8. 8
   workup.ADDITIONThis solid was carefully added to a coarse 500 mL frit
9. 9
   أخرىdried
10. 10
    غسيلMinimal washing with ice cold hexane
11. 11
    أخرىThe final compound was collected

الإجراء التجريبي

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.

المصدر