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

HRID 1954851Notes

Reaction equation

HRID 1954851 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 of 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. customwas hydrogenated at atmospheric pressure and room temperature of 4.5 h
  2. filtrationThe mixture was filtered through Celite (diatomaceous earth)
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-edcb6a4d1e2844c7900031d5bac2d731
Source dataset
uspto-grants-2000_09
Patent number
US06124284

Reaction notes

Loading…