Ethyl Acetate → 2-(3,4-dihydroxyphenyl)-5,6,7,8-tetramethoxychromen-4-one

HRID 371409Notes

Reaction equation

HRID 371409 reaction equation
C(OCC)(=O)C.C([O:14][C:15]1[CH:16]=[C:17]([CH:37]=[CH:38][C:39]=1[O:40]CC1C=CC=CC=1)[C:18]1[O:19][C:20]2[C:25]([C:26](=[O:28])[CH:27]=1)=[C:24]([O:29][CH3:30])[C:23]([O:31][CH3:32])=[C:22]([O:33][CH3:34])[C:21]=2[O:35][CH3:36])C1C=CC=CC=1>[Pd].CO>[OH:14][C:15]1[CH:16]=[C:17]([CH:37]=[CH:38][C:39]=1[OH:40])[C:18]1[O:19][C:20]2[C:25]([C:26](=[O:28])[CH:27]=1)=[C:24]([O:29][CH3:30])[C:23]([O:31][CH3:32])=[C:22]([O:33][CH3:34])[C:21]=2[O:35][CH3:36]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 13469722HCID 13469722, compound

Product 1

HCID 53180412-(3,4-dihydroxyphenyl)-5,6,7,8-tetramethoxychromen-4-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Into 200 ml. of a mixed solvent of ethyl acetate and methanol at a ratio of 1:1 was dissolved 1.11 g. of 3',4'-bis(benzyloxy)-5,6,7,8-tetramethoxyflavone and added 0.2 to 0.3 g. of 10% palladium-charcoal. The resulting mixture was mixed with shaking in a stream of H2 gas until H2 absorption was completed. After filtering out the catalyst, the obtained filtrate was concentrated. The residue was recrystallized from methanol to give 0.74 g. (97% of the theoretical amount) of the desired compound being a colorless prismatic crystal.

Workup

  1. additionThe resulting mixture was mixed
  2. filtrationAfter filtering out the catalyst
  3. concentrationthe obtained filtrate was concentrated
  4. customThe residue was recrystallized from methanol
  5. customto give 0.74 g

Sources & evidence

ORD record
ord-0c6f07addedb4cc88290cb8017113952
Source dataset
uspto-grants-1985_07
Patent number
US04532254

Reaction notes

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