Water → (3-Trifluoromethoxyphenyl)oxoacetaldehyde

HRID 2359418Notes

Reaction equation

HRID 2359418 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:5]=[C:6]([C:10](=[O:12])[CH3:11])[CH:7]=[CH:8][CH:9]=1.[OH2:15]>O1CCOCC1>[O:12]=[C:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([O:3][C:2]([F:13])([F:14])[F:1])[CH:5]=1)[CH:11]=[O:15]

Participants

4

Reactant 2

HCID 962WaterHCID 7371611-(3-(Trifluoromethoxy)phenyl)ethanone

Product 1

HCID 22273598(3-Trifluoromethoxyphenyl)oxoacetaldehydeYield 98%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1-(3-(trifluoromethoxy)phenyl)ethanone (5.0 g, 24.6 mmol) dissolved in 1,4-dioxane (75 mL) and water (4 mL) was added SeO2 (4.38 g, 39.4 mmol) in one portion. The mixture was refluxed overnight. The mixture was filtered to remove the black precipitate. The filtrate was concentrated and purified by column chromatography (1:5 Ethyl Acetate/Pentane) to give 2-oxo-2-(3-(trifluoromethoxy)phenyl)acetaldehyde as a yellow oil (5.3 g, 98% yield).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. filtrationThe mixture was filtered
  3. customto remove the black precipitate
  4. concentrationThe filtrate was concentrated
  5. custompurified by column chromatography (1:5 Ethyl Acetate/Pentane)

Sources & evidence

ORD record
ord-9bbac2328d554327add592f09c2cff6a
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

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