N-[4-(hydroxymethyl)-3-methylphenyl]acetamide → N-(4-Formyl-3-methylphenyl)acetamide

HRID 644730Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 644730
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:12])[CH3:11])=[CH:5][C:4]=1[CH3:13]>C(#N)C.[O-2].[O-2].[Mn+4]>[CH:2]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:12])[CH3:11])=[CH:5][C:4]=1[CH3:13])=[O:1]

Komponenten

4

Edukt 1

HCID 54053024N-[4-(hydroxymethyl)-3-methylphenyl]acetamide

Produkt 1

HCID 12931765N-(4-Formyl-3-methylphenyl)acetamideAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418406HCID 178418406, VerbindungKatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

N-[4-(Hydroxymethyl)-3-methylphenyl]acetamide (D77) (0.36 g, 2 mmol) and manganese dioxide (0.875 g, 10 mmol) were combined in acetonitrile (16 mL) and heated to 120° C. in the microwave for 7 minutes. The MnO2 was filtered off and the reaction mixture was concentrated to give the crude product which was purified by column chromatography. Elution with 0-100% ethyl acetate/petroleum ether yielded the title compound as a cream solid (0.326 g). δH (CDCl3, 400 MHz) 10.17 (1H, s), 7.77 (1H, d), 7.51 (1H, d), 7.45 (1H, s), 7.36 (1H, br.s), 2.66 (3H, s), 2.22 (3H, s). MS (ES): MH+ 178.2.

Aufarbeitung

  1. filtrationThe MnO2 was filtered off
  2. concentrationthe reaction mixture was concentrated
  3. customto give the crude product which
  4. customwas purified by column chromatography
  5. washElution with 0-100% ethyl acetate/petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-f747859b9e824acf989c8331146d1106
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700599B2

Notizen zur Reaktion

Wird geladen…