(4-Bromophenyl)(cyclohexyl)methanol → (4-Bromophenyl)(cyclohexyl)methanone

HRID 535319Notes

Reaction equation

HRID 535319 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[OH:9])=[CH:4][CH:3]=1>C(Cl)Cl.C(OCC)(=O)C.[O-2].[O-2].[Mn+4]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]2)=[O:9])=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 11402947(4-Bromophenyl)(cyclohexyl)methanol

Product 1

HCID 24261645(4-Bromophenyl)(cyclohexyl)methanone

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (4-bromophenyl)(cyclohexyl)methanol (3.45 g, 12.82 mmol) in DCM (100 ml) was added manganese dioxide (11.14 g, 128 mmol) at room temperature. The reaction mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate and the organic phase was washed with aqueous NaHCO3 solution and brine. The organic phase was dried over Na2SO4, filtered and concentrated in vacuo to obtain the title compound as slightly orange solid.

Workup

  1. washthe organic phase was washed with aqueous NaHCO3 solution and brine
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-279e421d6ef94f209b79a09dccf00dc1
Source dataset
uspto-grants-2014_10
Patent number
US08859535B2

Reaction notes

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