2-(3,4-Dimethoxyphenyl)-7-hydroxy-5,6-dimethoxychromen-4-one → Eupatilin

HRID 377351Notes

Reaction equation

HRID 377351 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:22])[CH:7]=[C:8]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=3)[O:9]2)=[C:4]([O:23]C)[C:3]=1[O:25][CH3:26].[Cl-].[Cl-].[Cl-].[Al+3]>C(#N)C>[OH:23][C:4]1[C:3]([O:25][CH3:26])=[C:2]([OH:1])[CH:11]=[C:10]2[C:5]=1[C:6](=[O:22])[CH:7]=[C:8]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=1)[O:9]2

Participants

4

Reactant 2

HCID 54916432-(3,4-Dimethoxyphenyl)-7-hydroxy-5,6-dimethoxychromen-4-oneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 5273755EupatilinYield 74.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

After 7-hydroxy-3',4',5,6-tetramethoxy flavone (4.44 g, 12.4 mmol) was suspended in 88 mL of acetonitrile and aluminum trichloride (8.27 g, 5 equivalents) was added hereto at room temperature, the reaction mixture was refluxed for 1.5 hour and the solvent was removed by evaporation under reduced pressure. To the residue was added 10% aqueous solution of hydrochloric acid and chloroform, then the solution was refluxed until it became clear. After the solution was cooled to room temperature, the organic layer was washed with water and brine, then dried over anhydrous magnesium sulfate and the solvent of the organic layer was removed by reduced pressure. The residue was recrystallized in methanol to afford 3.18 g of the product (74%).

Workup

  1. temperaturethe reaction mixture was refluxed for 1.5 hour
  2. customthe solvent was removed by evaporation under reduced pressure
  3. additionTo the residue was added 10% aqueous solution of hydrochloric acid and chloroform
  4. temperaturethe solution was refluxed until it
  5. washthe organic layer was washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent of the organic layer was removed by reduced pressure
  8. customThe residue was recrystallized in methanol

Sources & evidence

ORD record
ord-b2db93f7b6184ac6a5729904546705ce
Source dataset
uspto-grants-2000_02
Patent number
US06025387

Reaction notes

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