2-(3,4-Dimethoxyphenyl)-5,6-dimethoxy-7-(phenylmethoxy)-4H-1-benzopyran-4-one → 2-(3,4-Dimethoxyphenyl)-7-hydroxy-5,6-dimethoxychromen-4-one

HRID 377350Notes

Reaction equation

HRID 377350 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=[O:29])[CH:14]=[C:15]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=3)[O:16]2)=[C:11]([O:30][CH3:31])[C:10]=1[O:32][CH3:33])C1C=CC=CC=1>C(Cl)(Cl)Cl.[Pd]>[OH:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=[O:29])[CH:14]=[C:15]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=3)[O:16]2)=[C:11]([O:30][CH3:31])[C:10]=1[O:32][CH3:33]

Participants

4

Reactant 1

HCID 138738182-(3,4-Dimethoxyphenyl)-5,6-dimethoxy-7-(phenylmethoxy)-4H-1-benzopyran-4-one

Product 1

HCID 54916432-(3,4-Dimethoxyphenyl)-7-hydroxy-5,6-dimethoxychromen-4-oneYield 99.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6212ChloroformSolvent

Procedure

7-benzyloxy-3',4',5,6-tetramethoxy flavone (5.62 g, 12.5 mmol) was dissolved in chloroform, hereto was added 10% Pd/C (1.06 g, 0.08 equivalents) and the mixture was stirred under hydrogen atmosphere at room temperature. After the reaction was completed, the reaction mixture was filtered through celite pad and the solvent was removed by evaporation to give 4.44 g of the titled product (98%).

Workup

  1. filtrationthe reaction mixture was filtered through celite pad
  2. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-ab8d246ae70841cc885f018e8dc3861a
Source dataset
uspto-grants-2000_02
Patent number
US06025387

Reaction notes

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