P-Anisidine → N-(4-Methoxyphenyl)Acetamide

HRID 250784

Reaktionsgleichung

Reaktionsgleichung von HRID 250784
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1>ClCCl>[C:1]([NH:16][C:13]1[CH:14]=[CH:15][C:10]([O:9][CH3:8])=[CH:11][CH:12]=1)(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 7732P-AnisidineHCID 7918Acetic Anhydride

Produkt 1

HCID 5827N-(4-Methoxyphenyl)AcetamideAusbeute 96,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Acetic anhydride (16.0 mL, 169 mmol) was added dropwise over 1 h to a mixture of p-anisidine (20.0 g, 162 mmol) and dichloromethane (60 mL), with moderation by cooling in a water bath. The mixture was stirred at room temperature for 1 h, during which time a solid formed. Petroleum spirit (190 mL) was added, and the mixture was stirred for a further 1 h. The mixture was filtered and washed with petroleum spirit to afford 4-acetamidoanisole as a pale grey solid (25.8 g, 96%), m.p. 127-128° C. 1H NMR (399.7 MHz, CDCl3) δ 2.13, 3.78 (2 s, 2×3H, 2×CH3); 6.83 (app. d, 2H, J=8.8 Hz, BB′); 7.38 (app. d, 2H, J=8.8 Hz, AA′); 7.59 (br s, 1H, NH).

Aufarbeitung

  1. temperatureby cooling in a water bath
  2. customformed
  3. stirringthe mixture was stirred for a further 1 h
  4. filtrationThe mixture was filtered
  5. washwashed with petroleum spirit

Quellen und Nachweise

ORD-Eintrag
ord-01bf7b673f0b4bc992b819430d6de6ad
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863323B1

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