Toluene → 4-Vinylcyclohexane-carbaldehyde

HRID 1977011Notes

Reaction equation

HRID 1977011 reaction equation
[CH:1]([CH:3]1[CH2:8][CH2:7][CH:6]([CH2:9][OH:10])[CH2:5][CH2:4]1)=[CH2:2].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C1(C)C=CC=CC=1>ClCCl>[CH:1]([CH:3]1[CH2:8][CH2:7][CH:6]([CH:9]=[O:10])[CH2:5][CH2:4]1)=[CH2:2]

Participants

5

Reactant 3

HCID 1140TolueneHCID 155092854-VinylcyclohexylcarbinolHCID 178418287HCID 178418287, compound

Product 1

HCID 155092864-Vinylcyclohexane-carbaldehydeYield 39.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Next, 15 ml of solution of 5.4 g of the crude 4-vinyl-1-hydroxymethylcyclohexane in dichloromethane was added dropwise to a mixture of 9.1 g (42.1 mmol) of pyridinium chlorochromate and 50 ml of dichloromethane while being cooled with ice and stirred for 12 hours. The reaction mixture was filtered, the solvent was distilled off under a reduced pressure, and the residue thus obtained was subjected to silica gel column chromatography (eluent: toluene) to obtain 2.1 g of a crude 4-vinylcyclohexane-carbaldehyde. As the result of analysis of this product by gas chromatography, it was found out to be a mixture of cis/trans=31/69.

Workup

  1. temperaturewhile being cooled with ice
  2. filtrationThe reaction mixture was filtered
  3. distillationthe solvent was distilled off under a reduced pressure
  4. customthe residue thus obtained

Sources & evidence

ORD record
ord-931b694eea084324b7cebd581b091616
Source dataset
uspto-grants-2001_05
Patent number
US06231934B1

Reaction notes

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