2-(3,4-Dimethoxyphenyl)-7-hydroxy-5,6-dimethoxychromen-4-one → Eupatilin
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]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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%).