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

HRID 1349365Notes

Reaction equation

HRID 1349365 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-721a7503315d425999f6759b7a86ae89
Source dataset
uspto-grants-2007_05
Patent number
US07211680B2

Reaction notes

Loading…