3-(4-Fluorophenyl)-2-propenoic acid → 3-(4-Fluorophenyl)propionic acid

HRID 362804

Reaction equation

HRID 362804 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1>[Pd].C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])=[CH:11][CH:12]=1

Participants

4

Reactant 1

HCID 980703-(4-Fluorophenyl)-2-propenoic acid

Product 1

HCID 1363023-(4-Fluorophenyl)propionic acidYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-fluorocinnamic acid (300.0 g, 1.8 mol, Aldrich) and 5% palladium on carbon (9.0 g) in ethanol (3 L) was hydrogenated at atmospheric pressure and room temperature for 4.5 h. The mixture was filtered through Celite (diatomaceous earth) and the filtrate was concentrated in vacuo to give 275.1 g (91%) of 3-(4-fluorophenyl)propionic acid as a white solid: m.p., 86°-88° C.;

Workup

  1. filtrationThe mixture was filtered through Celite (diatomaceous earth)
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-9fffec0f198b4e048795124dd3fd9a26
Source dataset
uspto-grants-1999_02
Patent number
US05872118

Linked notes

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