Acetic Anhydride → 4'-Acetoxy-5-hydroxy-3,3',7-trimethoxyflavone

HRID 223127

Reaktionsgleichung

Reaktionsgleichung von HRID 223127
[OH:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]2[O:7][C:8]3[C:13]([C:14](=[O:18])[C:15]=2[O:16][CH3:17])=[C:12]([OH:19])[CH:11]=[C:10]([O:20][CH3:21])[CH:9]=3)=[CH:4][C:3]=1[O:24][CH3:25].[C:26]([O-])(=[O:28])[CH3:27].[Na+].C(OC(=O)C)(=O)C>>[C:26]([O:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]2[O:7][C:8]3[C:13]([C:14](=[O:18])[C:15]=2[O:16][CH3:17])=[C:12]([OH:19])[CH:11]=[C:10]([O:20][CH3:21])[CH:9]=3)=[CH:4][C:3]=1[O:24][CH3:25])(=[O:28])[CH3:27]

Komponenten

4

Edukt 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 5281677Pachypodol

Produkt 1

HCID 205225554'-Acetoxy-5-hydroxy-3,3',7-trimethoxyflavoneAusbeute 90 %

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 250 mg of 4',5-dihydroxy-3,3',7-trimethoxyflavone, 60 mg of sodium acetate and 70 mg of acetic anhydride was heated at 100° C. for 2 hours. The reaction mixture was evaporated under reduced pressure, and the residue was extracted with 30 ml of chloroform. Removal of the solvent from the extract and subsequent recrystallization of the residue from methanol gave 250 mg (90% yield) of 4'-acetoxy-5-hydroxy-3,3',7-trimethoxyflavone as yellow crystals: m.p. 168°-169° C.

Aufarbeitung

  1. customThe reaction mixture was evaporated under reduced pressure
  2. extractionthe residue was extracted with 30 ml of chloroform
  3. customRemoval of the solvent from the
  4. extractionextract
  5. customsubsequent recrystallization of the residue from methanol

Quellen und Nachweise

ORD-Eintrag
ord-1f8793b850b9462e8558abd9f4b2a09e
Quelldatensatz
uspto-grants-1982_10
Patentnummer
US04352792

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