3-(4-Methylphenyl)but-3-en-2-ol → 3-(4-Methylphenyl)-3-buten-2-one
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]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
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
- filtrationfiltered on Celite
- 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
- customare obtained as colorless oils
Sources & evidence
- ORD record
- ord-1dd1fd949e9349d4a4adc2e68ca000a1
- Source dataset
- uspto-grants-2003_07
- Patent number
- US06600058B1
Reaction notes
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