Potassium Carbonate → 7-methoxy-3-(4-methoxyphenyl)-2H-chromen-2-one

HRID 1267766Notes

Reaction equation

HRID 1267766 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21](Cl)=[O:22])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:11][O:10][C:8]1[CH:9]=[C:2]2[C:3]([CH:4]=[C:20]([C:17]3[CH:18]=[CH:19][C:14]([O:13][CH3:12])=[CH:15][CH:16]=3)[C:21](=[O:22])[O:1]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 696002-Hydroxy-4-MethoxybenzaldehydeHCID 27346884-Methoxyphenylacetyl chloride

Product 1

HCID 6889737-methoxy-3-(4-methoxyphenyl)-2H-chromen-2-oneYield 89.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 2-hydroxy-4-methoxybenzaldehyde (6.10 g), 4-methoxyphenylacetylchloride (11.1 g) and potassium carbonate (20 g) in acetone (400 ml) was heated under reflux for 2 hours. The reaction mixture was evaporated to remove the solvent, followed by addition of water. The resulting precipitates were collected by filtration and dried under reduced pressure to give 7-methoxy-3-(4-methoxyphenyl)-chromen-2-one (10.1 g, Yield 89%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customThe reaction mixture was evaporated
  4. customto remove the solvent
  5. additionfollowed by addition of water
  6. customThe resulting precipitates
  7. filtrationwere collected by filtration
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-f689324d1e8e4013bebc513e8b197ca4
Source dataset
uspto-grants-2003_04
Patent number
US06552068B1

Reaction notes

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