3-Trifluoromethylcinnamic acid → 3-(3-Trifluoromethylphenyl)propanoic acid

HRID 1172593Notes

Reaction equation

HRID 1172593 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]([OH:13])=[O:12])[CH:6]=[CH:7][CH:8]=1>CO.[Pd]>[F:1][C:2]([F:14])([F:15])[C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 855273-Trifluoromethylcinnamic acid

Product 1

HCID 27776833-(3-Trifluoromethylphenyl)propanoic acidYield 86.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In an inert atmosphere, Pd—C (10%, 2.84 g) was suspended in methanol (130 ml) followed by the addition of a solution of 3-(3-trifluoromethyl-phenyl)-acrylic acid (14.21 g, 65.7 mmol). The reaction mixture was put under an atmosphere of hydrogen (1 bar) and vigorously stirred for 2.5 h. The reaction mixture was filtered over a pad of celite and concentrated under reduced pressure to give 12.39 g (86%) of 3-(3-trifluoromethyl-phenyl)-propionic acid. LC-MS: tR=0.87 min; [M+H]+=no ionisation.

Workup

  1. filtrationThe reaction mixture was filtered over a pad of celite
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-30eedd39136c4cb5aab5adb00971546a
Source dataset
uspto-grants-2010_11
Patent number
US07834028B2

Reaction notes

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