3-[4-(1-Methylethyl)phenyl]-3-buten-2-ol → 3-[4-(1-Methylethyl)phenyl]-3-buten-2-one
Reaction equation
[CH3:1][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[CH2:14])[CH:11]([OH:13])[CH3:12])=[CH:6][CH:5]=1)[CH3:3]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:3][CH:2]([C:4]1[CH:5]=[CH:6][C:7]([C:10](=[CH2:14])[C:11](=[O:13])[CH3:12])=[CH:8][CH:9]=1)[CH3:1]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
2.75 g of alcohol 45 is dissolved in 300 ml of methylene chloride, and 25.1 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 937 mg of title compound 46 in addition to 635 mg of the starting material is obtained as colorless oils.
Workup
- filtrationfiltered on Celite
- customthe residue is chromatographed on silica gel with ethyl acetate/hexane, whereby 937 mg of title compound 46 in addition to 635 mg of the starting material
- customis obtained as colorless oils
Sources & evidence
- ORD record
- ord-46670eeb990f4cc4b4c766c888a6dd76
- Source dataset
- uspto-grants-2003_09
- Patent number
- US06613920B1
Reaction notes
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