1-[4-(Diethoxymethyl)phenyl]-3,3-dimethylbutan-1-ol → 1-[4-(Diethoxymethyl)-phenyl]-3,3-dimethylbutan-1-one

HRID 911701Notes

Reaction equation

HRID 911701 reaction equation
[CH2:1]([O:3][CH:4]([O:18][CH2:19][CH3:20])[C:5]1[CH:10]=[CH:9][C:8]([CH:11]([OH:17])[CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:7][CH:6]=1)[CH3:2]>CCCCCC.[O-2].[O-2].[Mn+4]>[CH2:19]([O:18][CH:4]([O:3][CH2:1][CH3:2])[C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:17])[CH2:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[CH:7][CH:6]=1)[CH3:20]

Participants

4

Reactant 1

HCID 576563551-[4-(Diethoxymethyl)phenyl]-3,3-dimethylbutan-1-ol

Product 1

HCID 576563621-[4-(Diethoxymethyl)-phenyl]-3,3-dimethylbutan-1-oneYield 93%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8058HexaneSolvent

Procedure

Dissolve 1-[4-(diethoxymethyl)-phenyl]-3,3-dimethylbutan-1-ol (3.8 g, 13.57 mmol) in hexane (50 mL). Add manganese dioxide (3.5 g, 40.71 mmol) and stir the mixture at 60° C. overnight. Filter the solid and concentrate the filtrate in vacuo to give the desired intermediate as a colorless oil (3.49 g, 93%).

Workup

  1. filtrationFilter the solid
  2. concentrationconcentrate the filtrate in vacuo

Sources & evidence

ORD record
ord-937eb670761b4d08a9adbc9a7ac430b5
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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