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

HRID 1816567Notes

Reaction equation

HRID 1816567 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6].P([O-])(O)(O)=[O:16].[Na+].Cl([O-])=O.[Na+].O>CS(C)=O>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:8]=[CH:7][C:4]=1[C:5]([OH:16])=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 49847042-Methoxy-4-(trifluoromethyl)benzaldehydeHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 36908732-Methoxy-4-(trifluoromethyl)benzoic acidYield 27.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3.0 g of 2-methoxy-4-(trifluoromethyl)benzaldehyde was dissolved in 50 ml dimethyl sulfoxide and an aqueous solution (20 ml) of 1.6 g sodium dihydrogenphosphate, followed by adding dropwise an aqueous solution (30 ml) of 8.0 g sodium chlorite thereinto. After stirring at room temperature for 3 days, 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, to give 0.8 g of 2-methoxy-4-(trifluoromethyl)benzoic acid as a colorless solid from fractions eluted with hexane-ethyl acetate (3:7).

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

Sources & evidence

ORD record
ord-1c533168a8c647c0a16ba9cbf476a93b
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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