Acetone → Chromen-4-one, 3,5,7-trimethoxy-2-phenyl-

HRID 1108290Notes

Reaction equation

HRID 1108290 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([C:7]2[O:17][C:16]3[CH:15]=[C:14](O)[CH:13]=[C:12](O)[C:11]=3[C:9](=[O:10])[C:8]=2[OH:20])=[CH:5][CH:6]=1.[C:21](=[O:24])([O-])[O-].[K+].[K+].S([O:32][CH3:33])(OC)(=O)=O.[CH3:34]C(C)=O>>[CH3:34][O:20][C:8]1[C:9](=[O:10])[C:11]2[C:16](=[CH:15][C:14]([O:24][CH3:21])=[CH:13][C:12]=2[O:32][CH3:33])[O:17][C:7]=1[C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 5281616Galangin

Product 1

HCID 117900Chromen-4-one, 3,5,7-trimethoxy-2-phenyl-Yield 67%

Procedure

Galangin (27 mg, 0.1 mmol) was dissolved in dried acetone (20 mL), solid potassium carbonate (0.5 g) and dimethyl sulfate (1 mL) were added, and the mixture was refluxed for 4 hrs, then cooled to room temperature. The solution was filtered and evaporated, water (20 mL) and concentrated ammonium hydroxide (2 mL) were added and the solution was extracted with ethyl acetate (15 mL×2). The solvent was evaporated and the residue was recrystallized from methanol/water to give 21 mg product (67%). 1HNMR (DMSO-d6): d 3.73 (s, 3H, 3-OCH3), 3.86 (s, 3H, 7-OCH3), 3.86 (s, 3H, 5-OCH3), 6.48 (s, 1H, 8-H), 6.79 (s, 1H, 6-H), 7,99 (m, 3H), 8.02 (m, 2H). MS (CI/NH3): m/z 313 (MH+, base).

Workup

  1. temperaturethe mixture was refluxed for 4 hrs
  2. filtrationThe solution was filtered
  3. customevaporated
  4. additionwater (20 mL) and concentrated ammonium hydroxide (2 mL) were added
  5. extractionthe solution was extracted with ethyl acetate (15 mL×2)
  6. customThe solvent was evaporated
  7. customthe residue was recrystallized from methanol/water

Sources & evidence

ORD record
ord-71c76eb9b3b042979f48db7710450ca9
Source dataset
uspto-grants-2000_05
Patent number
US06066642

Reaction notes

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