Methyl vinyl ketone → 1-(2H-1-Benzopyran-3-yl)ethanone

HRID 1110417Notes

Reaction equation

HRID 1110417 reaction equation
[CH:1](=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[O:10]=[C:11]([CH3:14])[CH:12]=[CH2:13].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[C:11]([C:12]1[CH2:13][O:4][C:3]2[C:2]([CH:1]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2)(=[O:10])[CH3:14]

Participants

5

Reactant 3

HCID 6570Methyl vinyl ketoneHCID 6998SalicylaldehydeHCID 11430Potassium Carbonate

Product 1

HCID 400671-(2H-1-Benzopyran-3-yl)ethanone

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

1.22 g (10 mmol) of salicylaldehyde together with 0.66 g (10 mmol) of 3-oxo-1-butene are added at room temperature to a suspension of 0.14 g (1 mmol) of potassium carbonate in 50 ml of 2™butanone. The mixture is brought to reflux with stirring and this temperature is maintained for 4 hours. The reaction medium is evaporated on a water bath under vacuum and the residue taken up with 100 ml of water and extracted three times with 75 ml of diethyl ether. The organic phases are combined, washed to neutrality with saturated aqueous sodium chloride solution, dried over sodium sulfate and filtered, the filtrate is evaporated on a water bath under vacuum and the product recrystallized in hexane

Workup

  1. temperatureto reflux
  2. temperaturethis temperature is maintained for 4 hours
  3. customThe reaction medium is evaporated on a water bath under vacuum
  4. extractionextracted three times with 75 ml of diethyl ether
  5. washwashed to neutrality with saturated aqueous sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe filtrate is evaporated on a water bath under vacuum
  9. customthe product recrystallized in hexane

Sources & evidence

ORD record
ord-094515ef93994374a686e618ada6815d
Source dataset
uspto-grants-1990_12
Patent number
US04975455

Reaction notes

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