Water → 3-Cyano-5-(trifluoromethyl)benzoic acid

HRID 906334Notes

Reaction equation

HRID 906334 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.O>CC(C)=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 3

HCID 962WaterHCID 117012213-(Hydroxymethyl)-5-(trifluoromethyl)benzonitrileHCID 131709961Jones' reagent

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

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), the solution was added with 2 M Jones reagent (26.8 mL, 53.6 mmol), and the mixture was stirred for 12 hours. The reaction mixture was added with water (15 mL) for dilution, 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 added with 1 M hydrochloric acid for neutralization, and extracted with chloroform. The organic layer was washed with saturated brine, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 3-cyano-5-(trifluoromethyl)benzoic acid (2.44 g, 85%) as colorless solid.

Workup

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

Sources & evidence

ORD record
ord-1020da68b067414f8195b3f801464dc6
Source dataset
uspto-grants-2011_09
Patent number
US08012989B2

Reaction notes

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