Ethanol → 3-[4-Methoxy-3-(trifluoromethyl)phenyl]propionic acid

HRID 452591Notes

Reaction equation

HRID 452591 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]([OH:13])=[O:12])=[CH:5][C:4]=1[C:14]([F:17])([F:16])[F:15].C(O)C>[Pd].O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:5][C:4]=1[C:14]([F:15])([F:17])[F:16]

Participants

5

Reactant 2

HCID 702EthanolHCID 534016853-[4-Methoxy-3-(trifluoromethyl)phenyl]acrylic acid

Product 1

HCID 573635703-[4-Methoxy-3-(trifluoromethyl)phenyl]propionic acidYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-[4-methoxy-3-(trifluoromethyl)phenyl]acrylic acid (2.90 g, 11.8 mmol), 10% palladium on carbon (250 mg), ethanol (60 mL) and tetrahydrofuran (40 mL) was stirred under a hydrogen atmosphere (1 kg/cm2) at room temperature overnight. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-0/1) to give the title compound (2.40 g, yield 83%) as colorless crystals.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-0/1)

Sources & evidence

ORD record
ord-68d533c849884445996d092681d4de12
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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