3-(Hydroxymethyl)-5-(trifluoromethyl)benzonitrile → 3-Cyano-5-(trifluoromethyl)benzoic acid

HRID 1442517Notes

Reaction equation

HRID 1442517 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:6]#[N:7].CC(C)=[O:17].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O.O>[C:6]([C:5]1[CH:4]=[C:3]([CH:10]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:8]=1)[C:2]([OH:17])=[O:1])#[N:7]

Participants

5

Reactant 2

HCID 117012213-(Hydroxymethyl)-5-(trifluoromethyl)benzonitrileHCID 131709961Jones' reagent

Product 1

HCID 589022873-Cyano-5-(trifluoromethyl)benzoic acidYield 85%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

3-(Hydroxymethyl)-5-(trifluoromethyl)benzonitrile (2.70 g, 13.4 mmol) synthesized by the method described in Japanese Patent Unexamined Publication (Kokai) No. 2003-221376 was dissolved in acetone (30 mL), to the solution was added 2 M Jones reagent (26.8 mL, 53.6 mmol), and the mixture was stirred for 12 hours. The reaction mixture was diluted with water (15 mL), and then extracted with ether. The organic layers were combined, and inversely extracted with 2 M aqueous sodium hydroxide, and then the aqueous layer was neutralized with 1 M hydrochloric acid, and extracted with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 3-cyano-5-(trifluoromethyl)benzoic acid (2.44 g, 85%) as a colorless solid.

Workup

  1. extractionextracted with ether
  2. extractioninversely extracted with 2 M aqueous sodium hydroxide
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d4a158cda47340cbb9b2d9c61fee6081
Source dataset
uspto-grants-2010_02
Patent number
US07659271B2

Reaction notes

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