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

HRID 223127

Reaction equation

HRID 223127 reaction equation
[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]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 5281677Pachypodol

Product 1

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

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-1f8793b850b9462e8558abd9f4b2a09e
Source dataset
uspto-grants-1982_10
Patent number
US04352792

Linked notes

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