Methyl Ethyl Ketone → 2H-1-Benzopyran, 3-acetyl-6-methoxy-

HRID 1110418Notes

Reaction equation

HRID 1110418 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([CH:10]=1)[CH:8]=O.[O:11]=[C:12]([CH3:15])[CH:13]=[CH2:14].C(=O)([O-])[O-:17].[K+].[K+].CC(=O)CC>O>[CH3:1][O:2][C:3]1[CH:10]=[C:7]2[C:6](=[CH:5][CH:4]=1)[O:17][CH2:14][C:13]([C:12](=[O:11])[CH3:15])=[CH:8]2

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 6570Methyl vinyl ketoneHCID 11430Potassium CarbonateHCID 115693-Methoxybenzaldehyde

Product 1

HCID 424352H-1-Benzopyran, 3-acetyl-6-methoxy-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.52 g (10 mmol) of 2-hydroxy™5-methoxybenzaldehyde, 0.66 g of 3-oxo-1-butene and 1.4 g (10 mmol) of potassium carbonate are added at room temperature and with magnetic stirring to 40 ml of 2-butanone. The mixture is brought to reflux with stirring and this temperature is maintained for 2 hours. After being cooled, the reaction medium is poured into 100 ml of water and extracted 3 times with 100 ml of diethyl ether. The organic phases are combined, washed to neutrality with saturated aqueous sodium chloride solution and dried over sodium sulfate, and the organic phase is evaporated on a water bath under vacuum and the product recrystallized.

Workup

  1. temperatureto reflux
  2. temperaturethis temperature is maintained for 2 hours
  3. temperatureAfter being cooled
  4. extractionextracted 3 times with 100 ml of diethyl ether
  5. washwashed to neutrality with saturated aqueous sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. customthe organic phase is evaporated on a water bath under vacuum
  8. customthe product recrystallized

Sources & evidence

ORD record
ord-3a20b39db2df49509f82f27bfdabe7c4
Source dataset
uspto-grants-1990_12
Patent number
US04975455

Reaction notes

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