3-[4-(1-Methylethyl)phenyl]-3-buten-2-ol → 3-[4-(1-Methylethyl)phenyl]-3-buten-2-one

HRID 478151Notes

Reaction equation

HRID 478151 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

HCID 180008773-[4-(1-Methylethyl)phenyl]-3-buten-2-ol

Product 1

HCID 180008583-[4-(1-Methylethyl)phenyl]-3-buten-2-one

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

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

  1. filtrationfiltered on Celite
  2. 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
  3. customis obtained as colorless oils

Sources & evidence

ORD record
ord-243eb4226a1b40639642a35f8bed5be2
Source dataset
uspto-grants-2003_11
Patent number
US06642218B2

Reaction notes

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