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

HRID 862752Notes

Reaction equation

HRID 862752 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.; NMR (DMSO-d6): d12.15 (br s, 1H, COOH), 7.07-7.29 (m,4H, Ar), 2.81(t, 2H, CH2CO), 2.52 (t,2H, ArCH2).

Workup

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

Sources & evidence

ORD record
ord-e2827b6d1bb446188bda6706c0c4ef75
Source dataset
uspto-grants-1998_02
Patent number
US05719186

Reaction notes

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