(E)-3-(4-(trifluoromethyl)phenyl)prop-2-en-1-ol → 4-Carboxycinnamaldehyde

HRID 381429Notes

Reaction equation

HRID 381429 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:12]=[CH:11][C:6](/[CH:7]=[CH:8]/[CH2:9][OH:10])=[CH:5][CH:4]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[F:1][C:2]([F:13])([F:14])[C:3]1[CH:12]=[CH:11][C:6](/[CH:7]=[CH:8]/[CH:9]=[O:10])=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 10512285(E)-3-(4-(trifluoromethyl)phenyl)prop-2-en-1-ol

Product 1

HCID 111716284-CarboxycinnamaldehydeYield 90%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

In 30 ml of methylene chloride were dissolved 2.15 g of trans-4-(trifluoromethyl) cinnamyl alcohol, and 14 g of active manganese dioxide were added to the solution at 0° C., followed by stirring of the resulting mixture for 15 minutes and then stirring at room temperature for 2 hours. The solid was removed by filtration and the filtrate was concentrated to obtain a crystalline residue. The residue was recrystallized from a mixed solvent of benzene-hexane to obtain the title compound having a melting point of 60 to 61° C. in a yield of 90%.

Workup

  1. additionwere added to the solution at 0° C.
  2. stirringstirring at room temperature for 2 hours
  3. customThe solid was removed by filtration
  4. concentrationthe filtrate was concentrated
  5. customto obtain a crystalline residue
  6. customThe residue was recrystallized from a mixed solvent of benzene-hexane

Sources & evidence

ORD record
ord-1641e0b3ab334d64a81c21c6ba9b17ff
Source dataset
uspto-grants-2001_10
Patent number
US06306880B1

Reaction notes

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