Water → 3-(3-Trifluoromethylphenyl)propanoic acid

HRID 1411213Notes

Reaction equation

HRID 1411213 reaction equation
O.[F:2][C:3]([F:16])([F:15])[C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[CH:7]=[CH:8][C:9]([OH:11])=[O:10].[H][H]>[C].[Pd].C1(C)C=CC=CC=1>[F:2][C:3]([F:15])([F:16])[C:4]1[CH:5]=[C:6]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])[CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 962WaterHCID 855273-Trifluoromethylcinnamic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 27776833-(3-Trifluoromethylphenyl)propanoic acidYield 97.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 1140TolueneSolvent

Procedure

Palladium carbon (10%, 6 gm) was added to water (20 ml) and then added 3-(trifluoromethyl)cinnamic acid (100 gm) and toluene (1000 ml). The resulting contents were hydrogenated with hydrogen gas at a pressure of 4 kg at 45 to 50° C. for 2 hour 30 minutes. The reaction mass was then filtered through celite bed and the layers were separated. The organic layer was dried over sodium sulfate and the solvent was distilled off under reduced pressure to obtain 98.7 gm of 3-[3-(trifluoromethyl)phenyl]propionic acid.

Workup

  1. filtrationThe reaction mass was then filtered through celite bed
  2. customthe layers were separated
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-93ceebe7877e4b3c9e27c8d26becd225
Source dataset
uspto-grants-2014_12
Patent number
US08921606B2

Reaction notes

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