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

HRID 1110422Notes

Reaction equation

HRID 1110422 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-l-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 procedure is then as in Example 1, stage A. The final chromatography is replaced by a recrystallization in hexane.

Workup

  1. temperatureto reflux
  2. temperaturethis temperature is maintained for 4 hours
  3. customThe final chromatography is replaced by a recrystallization in hexane

Sources & evidence

ORD record
ord-55447b374b2745319a6f52cf6bf690b1
Source dataset
uspto-grants-1990_12
Patent number
US04975454

Reaction notes

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