Sodium Acetate → 6-Methoxy-2-methyl-3-phenyl-4H-chromen-4-one

HRID 239614

Reaktionsgleichung

Reaktionsgleichung von HRID 239614
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10](=[O:18])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C:19]([O-])(=O)[CH3:20].[Na+]>C(OC(=O)C)(=O)C>[CH3:9][O:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[O:1][C:19]([CH3:20])=[C:11]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:10]2=[O:18]

Komponenten

4

Edukt 2

HCID 517045Sodium AcetateHCID 27756071-(2-Hydroxy-5-methoxyphenyl)-2-phenylethanone

Produkt 1

HCID 665791676-Methoxy-2-methyl-3-phenyl-4H-chromen-4-oneAusbeute 68,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7918Acetic AnhydrideLösungsmittel

Versuchsvorschrift

Intermediate 20 (4 g, 16.51 mmoles) was taken in a RB flask and to this acetic anhydride (40 ml) and sodium acetate (9.48 g, 115.57 mmoles) were added and the mixture was refluxed for 12 h. After cooling to RT, the reaction mixture was quenched by the addition of ice cold water. The solid formed was filtered and washed with water. The product was dried under vacuum to afford the title compound as yellow solid (3 g, 68% yield). 1H-NMR (δ ppm, CDCl3, 400 MHz): δ 7.60(d, J=3.0 Hz, 1H), 7.45(t, J=7.1 Hz, 2H), 7.37(m, 2H), 7.29(m, 3H), 3.89(s, 3H).2.31(s, 3H).

Aufarbeitung

  1. additionwere added
  2. temperaturethe mixture was refluxed for 12 h
  3. customthe reaction mixture was quenched by the addition of ice cold water
  4. customThe solid formed
  5. filtrationwas filtered
  6. washwashed with water
  7. customThe product was dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-0765d842534943d4b4ec74ac697b09aa
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642607B2

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