3-(4-Methylphenyl)but-3-en-2-ol → 3-(4-Methylphenyl)-3-buten-2-one

HRID 1359547Notes

Reaction equation

HRID 1359547 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[CH2:12])[CH:9]([OH:11])[CH3:10])=[CH:4][CH:3]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[CH2:12])[C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 106308343-(4-Methylphenyl)but-3-en-2-ol

Product 1

HCID 180007733-(4-Methylphenyl)-3-buten-2-one

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

2.91 g of alcohol 39 is dissolved in 300 ml of methylene chloride, and 43.5 g of manganese dioxide is added under nitrogen. It is stirred overnight at room temperature, filtered on Celite, and the residue is chromatographed on silica gel with ethyl acetate/hexane, whereby 850 mg of title compound 40 in addition to 1.06 g of the starting material are obtained as colorless oils.

Workup

  1. filtrationfiltered on Celite
  2. customthe residue is chromatographed on silica gel with ethyl acetate/hexane, whereby 850 mg of title compound 40 in addition to 1.06 g of the starting material
  3. customare obtained as colorless oils

Sources & evidence

ORD record
ord-1dd1fd949e9349d4a4adc2e68ca000a1
Source dataset
uspto-grants-2003_07
Patent number
US06600058B1

Reaction notes

Loading…