(+/-)-3,3-Dimethyl-1-p-tolyl-butan-1-ol → 3,3-Dimethyl-1-(4-methylphenyl)butan-1-one

HRID 911443Notes

Reaction equation

HRID 911443 reaction equation
[CH3:1][C:2]([CH3:14])([CH3:13])[CH2:3][CH:4]([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)[OH:5]>CCCCCC.[O-2].[O-2].[Mn+4]>[CH3:1][C:2]([CH3:14])([CH3:13])[CH2:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([CH3:12])=[CH:10][CH:11]=1)=[O:5]

Participants

4

Reactant 1

HCID 57656593(+/-)-3,3-Dimethyl-1-p-tolyl-butan-1-ol

Product 1

HCID 178606563,3-Dimethyl-1-(4-methylphenyl)butan-1-oneYield 102.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8058HexaneSolvent

Conditions

Temperature
65 °C

Procedure

To a stirred solution of (±)-3,3-dimethyl-1-p-tolyl-butan-1-ol (2.15 g, 11.3 mmol) in hexane (30 mL) add manganese dioxide (2.94 g, 33.8 mmol) and heat the mixture overnight at 65° C. Cool to ambient temperature, filter the manganese salts, and concentrate in vacuo to give the desired intermediate as a colorless oil (2.2 g, 100%).

Workup

  1. temperatureCool to ambient temperature
  2. filtrationfilter the manganese salts
  3. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-162df2b746f34994a577980c984339c0
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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