Acetic Anhydride → N-(2-Methoxy-6-methylphenyl)acetamide

HRID 1351991

Reaktionsgleichung

Reaktionsgleichung von HRID 1351991
[CH3:1][C:2]1[C:3]([N+:10]([O-])=O)=[C:4]([O:8][CH3:9])[CH:5]=[CH:6][CH:7]=1.[O:13]1CC[CH2:15][CH2:14]1.C(OC(=O)C)(=O)C>C(O)C.[Pd].C(OCC)(=O)C>[CH3:9][O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[NH:10][C:14](=[O:13])[CH3:15]

Komponenten

7

Edukt 3

HCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 792913-Methyl-2-nitroanisole

Produkt 1

HCID 578995N-(2-Methoxy-6-methylphenyl)acetamideAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 3-methyl-2-nitroanisole (10.00 g, 59.8 mmol) in ethanol (60 mL)-tetrahydrofuran (60 mL) is added a 10% palladium on carbon (50% wet, 2.00 g), and the mixture is subjected to hydrogenation, and stirred at room temperature for 1.5 hour. After the reaction is completed, the reaction solution is filtered through celite, and the solvent is evaporated under reduced pressure. To a solution of the residue in ethyl acetate (110 ml) is added acetic anhydride (9.0 mL, 95.2 mmol), and the mixture is refluxed for 5 hours. The reaction solution is cooled with ice, and the precipitated solid is collected by filtration, and washed with hexane to give the title compound (9.28 g, yield: 87%).

Aufarbeitung

  1. filtrationthe reaction solution is filtered through celite
  2. customthe solvent is evaporated under reduced pressure
  3. temperaturethe mixture is refluxed for 5 hours
  4. temperatureThe reaction solution is cooled with ice
  5. filtrationthe precipitated solid is collected by filtration
  6. washwashed with hexane

Quellen und Nachweise

ORD-Eintrag
ord-a8980aba367247a4b77abe9594e32bea
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07217724B2

Verknüpfte Notizen

Wird geladen…