Water → 2-Ethoxy-4-(trifluoromethyl)benzoic acid

HRID 1816661Notes

Reaction equation

HRID 1816661 reaction equation
[CH2:1]([O:3][C:4]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:8][C:5]=1[CH:6]=[O:7])[CH3:2].P([O-])(O)(O)=[O:17].[Na+].Cl([O-])=O.[Na+].O>CS(C)=O>[CH2:1]([O:3][C:4]1[CH:11]=[C:10]([C:12]([F:13])([F:14])[F:15])[CH:9]=[CH:8][C:5]=1[C:6]([OH:17])=[O:7])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 224943382-Ethoxy-4-(trifluoromethyl)benzaldehydeHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 224943272-Ethoxy-4-(trifluoromethyl)benzoic acidYield 420.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

0.60 g of 2-ethoxy-4-(trifluoromethyl)benzaldehyde was dissolved in 5 ml dimethyl sulfoxide and an aqueous solution (1 ml) of 67 mg sodium dihydrogen phosphate, and an aqueous solution (3 ml) of 0.35 g sodium chlorite was added dropwise. After stirring at room temperature for 12 hours, water was added thereto, followed by extracting with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. The residue was subjected to silica gel column chromatography, and from fractions eluted with hexane-ethyl acetate (2:1), 0.55 g of 2-ethoxy-4-(trifluoromethyl)benzoic acid was obtained.

Workup

  1. extractionby extracting with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. washfrom fractions eluted with hexane-ethyl acetate (2:1)

Sources & evidence

ORD record
ord-8f3d9dbf5a744e679e92e7bcb0449b8c
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

Loading…