Réaction #66715

Équation de réaction

N-(3-Methoxy-phenyl)-acetamide

acetyl chloride

aluminum chloride

→

N-(4-Acetyl-3-methoxy-phenyl)-acetamide

Rendement 74.4%

Solvants

methylene chloride

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGwith stirring
2. 2
   workup.ADDITIONThe reaction mixture was poured into ice
3. 3
   workup.STIRRINGstirred 35 minutes
4. 4
   Filtrationfiltered
5. 5
   LavageThe solid was washed with water
6. 6
   ExtractionThe filtrate was extracted with EtOAc and solvent
7. 7
   Autrewas removed under reduced pressure

Mode opératoire

N-(3-Methoxy-phenyl)-acetamide (17.7 g, 107 mmol) in methylene chloride was cooled to zero degrees C., and acetyl chloride (19.0 ml, 268 mmol) was slowly added, followed by aluminum chloride (35.7 g, 268 mmol) in small portions over 15 min. The reaction mixture was stirred 15 minutes at zero degrees, then allowed to warm to room temperature with stirring. The reaction mixture was poured into ice, stirred 35 minutes, and filtered. The solid was washed with water. The filtrate was extracted with EtOAc and solvent was removed under reduced pressure. The combined solids gave N-(4-Acetyl-3-methoxy-phenyl)-acetamide (16.5 g., 74%) as a solid.

Source