(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 1601358Notes

Reaction equation

HRID 1601358 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 dissolved 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 for 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-13505df4953c4bdf96408844c010f214
Source dataset
uspto-grants-1999_11
Patent number
US05977152

Reaction notes

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