Réaction #417960

Équation de réaction

N-(3-Hydroxyphenyl)acetamide

butyryl chloride

→

title compound

Rendement 75.0%

3-acetamidophenyl butyrate

Rendement 75.0%

Solvants

water

pyridine

Conditions de réaction

Traitement

1. 1
   workup.WAITThe resulting crystalline suspension was left for 18 hrs
2. 2
   Autreethyl acetate (1:1, 1000 mL), the organic layer was separated
3. 3
   Lavagewashed with brine (3×1000 mL)
4. 4
   SéchageThe organic layer was dried over sodium sulfate
5. 5
   Concentrationconcentrated in vacuo at 70° C.
6. 6
   Autreto remove pyridine
7. 7
   TempératureUpon cooling the oil
8. 8
   workup.ADDITIONThis solid was carefully added to a coarse 500 mL frit
9. 9
   Autredried
10. 10
    LavageMinimal washing with ice cold hexane
11. 11
    AutreThe final compound was collected

Mode opératoire

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.

Source