HCID 12405143, compound → 4H-1-Benzopyran-4-one, 2-(4-hydroxyphenyl)-5,6,7-trimethoxy-

HRID 1095272Notes

Reaction equation

HRID 1095272 reaction equation
C([O:8][C:9]1[CH:31]=[CH:30][C:12]([C:13]2[O:14][C:15]3[C:20]([C:21](=[O:23])[CH:22]=2)=[C:19]([O:24][CH3:25])[C:18]([O:26][CH3:27])=[C:17]([O:28][CH3:29])[CH:16]=3)=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].C(O)C>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]2[O:14][C:15]3[C:20]([C:21](=[O:23])[CH:22]=2)=[C:19]([O:24][CH3:25])[C:18]([O:26][CH3:27])=[C:17]([O:28][CH3:29])[CH:16]=3)=[CH:30][CH:31]=1

Participants

4

Reactant 1

HCID 12405143HCID 12405143, compound

Product 1

HCID 2437594H-1-Benzopyran-4-one, 2-(4-hydroxyphenyl)-5,6,7-trimethoxy-Yield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a suspension of 1e 4′-benzyloxy-5,6,7-trimethoxyflavone, (120 mg, 0.29 mmol) and a catalytic amount of palladium on charcoal (10%) in ethanol (15 mL) was hydrogenated at atmospheric pressure for 4 h. The catalyst was filtered off and the solvent was stripped off to produce the title compound 1h (89 mg, 95%) as slight yellow crystals. Without purification, the purity of this compound is higher than 95%. 1H NMR (DMSO, 200 M Hz), δ 7.88 (d, J=8.6 Hz, 2H), 7.16 (s, 1H), 6.90 (d, J=8.6 Hz, 2H), 6.60 (s, 1H), 3.93 (s 3H), 3.93 (s, 3H), 3.78 (s, 3H), 3.75 (s, 3H).

Workup

  1. filtrationThe catalyst was filtered off

Sources & evidence

ORD record
ord-0e2e3039e21c457e99a49469f1bdf533
Source dataset
uspto-grants-2012_03
Patent number
US08138165B2

Reaction notes

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