4-tert-Butylcyclohexylmethanol → Cyclohexanecarboxaldehyde, 4-(1,1-dimethylethyl)-

HRID 653970

Reaction equation

HRID 653970 reaction equation
[CH3:1][C:2]([CH:5]1[CH2:10][CH2:9][CH:8]([CH2:11][OH:12])[CH2:7][CH2:6]1)([CH3:4])[CH3:3].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH3:4][C:2]([CH:5]1[CH2:6][CH2:7][CH:8]([CH:11]=[O:12])[CH2:9][CH2:10]1)([CH3:1])[CH3:3]

Participants

4

Reactant 2

HCID 827594-tert-ButylcyclohexylmethanolHCID 178418287HCID 178418287, compound

Product 1

HCID 88655Cyclohexanecarboxaldehyde, 4-(1,1-dimethylethyl)-Yield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(1,1-dimethylethyl)cyclohexanemethanol (1.0 g, 5.9 mmol) in CH2Cl2 (distilled from CaH2) (43 mL) were added at room temperature under argon anhydrous NaOAc (3.84 g, 46.8 mmol). After stirring at room temperature for 5 minutes pyridinium chlorochromate (3.84 g, 17.8 mmol) was added and after stirring for 1 h at room temperature, the reaction was quenched by addition of ethyl ether (200 mL). The crude reaction was filtered through a Fluorasil column to give crude 4-(1,1-dimethylethyl)cyclohexanecarboxaldehyde (0.862 g, 5.12 mmol) as a mixture of trans and cis isomer in 87% yield.

Workup

  1. additionwas added
  2. customthe reaction was quenched by addition of ethyl ether (200 mL)
  3. customThe crude reaction
  4. filtrationwas filtered through a Fluorasil column

Sources & evidence

ORD record
ord-021c9bf670ac429fbcb55df8c935b3f3
Source dataset
uspto-grants-1992_07
Patent number
US05128448

Linked notes

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