(2E,4E)-3-Methyl-5-[4-(trifluoromethyl)phenyl]-2,4-pentadien-1-ol → (2E,4E)-3-Methyl-5-[4-(trifluoromethyl)phenyl]-2,4-pentadienal

HRID 381421Notes

Reaction equation

HRID 381421 reaction equation
[CH3:1]/[C:2](/[CH:6]=[CH:7]/[C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1)=[CH:3]\[CH2:4][OH:5]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1]/[C:2](/[CH:6]=[CH:7]/[C:8]1[CH:9]=[CH:10][C:11]([C:14]([F:15])([F:16])[F:17])=[CH:12][CH:13]=1)=[CH:3]\[CH:4]=[O:5]

Participants

4

Reactant 1

HCID 59970560(2E,4E)-3-Methyl-5-[4-(trifluoromethyl)phenyl]-2,4-pentadien-1-ol

Product 1

HCID 59970538(2E,4E)-3-Methyl-5-[4-(trifluoromethyl)phenyl]-2,4-pentadienalYield 100.8%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

In 10 ml of methylene chloride were dissolveed 460 mg (1.90 mmol) of (2E,4E)-3-methyl-5-[4-(trifluoromethyl)phenyl]-2,4-pentadien-1-ol, and 5 g of active manganese dioxide were added to the mixture, followed by stirring of the resulting mixture at room temperature of 30 minutes. The solid was removed by filtration, and after the filtrate was concentrated, it was purified over silica gel chromatography (eluting solvent: 4% ethyl acetate-hexane) to obtain 460 mg of the title compound as an oil.

Workup

  1. additionwere added to the mixture
  2. customThe solid was removed by filtration
  3. concentrationafter the filtrate was concentrated
  4. customit was purified over silica gel chromatography (eluting solvent: 4% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-72e50a9f6913453ba94292313668549a
Source dataset
uspto-grants-2001_10
Patent number
US06306880B1

Reaction notes

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