4'-(Benzyloxy)-5-hydroxy-3,3',7-trimethoxyflavone → Pachypodol

HRID 223126Notes

Reaction equation

HRID 223126 reaction equation
C([O:8][C:9]1[CH:30]=[CH:29][C:12]([C:13]2[O:14][C:15]3[C:20]([C:21](=[O:25])[C:22]=2[O:23][CH3:24])=[C:19]([OH:26])[CH:18]=[C:17]([O:27][CH3:28])[CH:16]=3)=[CH:11][C:10]=1[O:31][CH3:32])C1C=CC=CC=1>C(O)C.[Pd]>[OH:8][C:9]1[CH:30]=[CH:29][C:12]([C:13]2[O:14][C:15]3[C:20]([C:21](=[O:25])[C:22]=2[O:23][CH3:24])=[C:19]([OH:26])[CH:18]=[C:17]([O:27][CH3:28])[CH:16]=3)=[CH:11][C:10]=1[O:31][CH3:32]

Participants

4

Reactant 1

HCID 205225384'-(Benzyloxy)-5-hydroxy-3,3',7-trimethoxyflavone

Product 1

HCID 5281677PachypodolYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 0.86 g of 4'-(benzyloxy)-5-hydroxy-3,3',7-trimethoxyflavone in 30 ml of ethanol was hydrogenated in the presence of 50 mg of 5% by weight palladium-charcoal at room temperature under atmospheric pressure. After 1 hour, the catalyst was filtered off and the filtrate was evaporated under reduced pressure. The residue was recrystallized from ethyl acetate/hexane. There was obtained 0.58 g (90% yield) of 4',5-dihydroxy-3,3',7-trimethoxyflavone as yellow crystals: m.p. 171°-173° C.

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-cae083b04b604fb787ca83968020b153
Source dataset
uspto-grants-1982_10
Patent number
US04352792

Reaction notes

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