Potassium Carbonate → HCID 21270184, compound

HRID 1194473Notes

Reaction equation

HRID 1194473 reaction equation
[OH:1][C:2]1[CH:19]=[CH:18][C:5]2[C:6](=[O:17])[C:7]([C:10]3[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=3)=[CH:8][O:9][C:4]=2[C:3]=1O.[C:21](=[O:24])([O-])[O-].[K+].[K+].S([O-])(O[CH3:31])(=O)=O>CC(C)=O>[CH3:31][O:1][C:2]1[CH:19]=[CH:18][C:5]2[C:6](=[O:17])[C:7]([C:10]3[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=3)=[CH:8][O:9][C:4]=2[C:3]=1[O:24][CH3:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4694097Methyl sulfate(1-)HCID 5481241HCID 5481241, compound

Product 1

HCID 21270184HCID 21270184, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

7,8-Dihydroxy-3-(4-methylphenyl)-4H-1-benzopyran-4-one (2.7 g), described in example 9, is dissolved in dry acetone (50 ml). Pyrolyzed potassium carbonate (4.14 g) is added and the mixture is heated to reflux. A solution of methyl sulphate (3.78 g) in acetone (10 ml) is then added dropwise and heating is maintained for three more hours. After cooling, the solid is filtered and the solution is evaporated to dryness under vacuum. Water is added to the residue which is filtered, washed with an aqueous sodium hydroxide solution (1N) then with water and dried. After crystallization in methanol, 7,8-dimethoxy-3-(4-methylphenyl)-4H-1-benzopyran-4-one is obtained, m.p. 135°.

Workup

  1. temperaturethe mixture is heated to reflux
  2. temperatureheating
  3. temperatureis maintained for three more hours
  4. temperatureAfter cooling
  5. filtrationthe solid is filtered
  6. customthe solution is evaporated to dryness under vacuum
  7. additionWater is added to the residue which
  8. filtrationis filtered
  9. washwashed with an aqueous sodium hydroxide solution (1N)
  10. dry with materialwith water and dried
  11. customAfter crystallization in methanol

Sources & evidence

ORD record
ord-2b5b1880c66d49e893a283b139f4345a
Source dataset
uspto-grants-1989_03
Patent number
US04814346

Reaction notes

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