Réaction #66717

Équation de réaction

ammonium formate

ammonium formate

N-[4-(1-Hydroxy-1-methyl-ethyl)-3-methoxy-phenyl]-acetamide

ammonium formate

→

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

Rendement 99.2%

Solvants

acetic acid

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction mixture was heated to reflux
2. 2
   TempératureReflux
3. 3
   workup.WAITwas continued for another hour
4. 4
   Températurethe reaction mixture was cooled
5. 5
   Filtrationfiltered through Celite
6. 6
   workup.ADDITIONThe filtrate was diluted with water
7. 7
   Extractionextracted with EtOAc
8. 8
   Lavagethe combined organic layers were washed with brine
9. 9
   Séchagedried over magnesium sulfate
10. 10
    AutreEvaporation under reduced pressure

Mode opératoire

N-[4-(1-Hydroxy-1-methyl-ethyl)-3-methoxy-phenyl]-acetamide (16.4 g) in 100 ml glacial acetic acid was stirred at room temperature under N2, and palladium on activated carbon (3 g 10 Wt %) was added, followed by 5 g of ammonium formate. The reaction mixture was heated to reflux. After 30 minutes 5 g ammonium formate was added, and after 45 minutes another 8.5 g ammonium formate was added. Reflux was continued for another hour, then the reaction mixture was cooled, and filtered through Celite. The filtrate was diluted with water, extracted with EtOAc, and the combined organic layers were washed with brine and dried over magnesium sulfate. Evaporation under reduced pressure gave N-(4-Isopropyl-3-methoxy-phenyl)-acetamide (15.1 g, 99%).

Source