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

HRID 1363673Notes

Reaction equation

HRID 1363673 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1>C1COCC1.[Rh]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:6][CH:7]=1

Participants

4

Reactant 1

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

Product 1

HCID 1363023-(4-Fluorophenyl)propionic acid

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3-(4-Fluoro-phenyl)-acrylic acid (25.00 g, 151.00 mmol) in THF was mixed with Rh/Al2O3 (1.00 g) and hydrogenated for 14 hours. The reaction mixture was filtered through celite and the filtrate was concentrated to give 3-(4-fluoro-phenyl)-propionic acid. 3-(4-fluoro-phenyl)-propionic acid was then reacted with SOCl2 (16.50 mL, 0.23 mol) and AlCl3 (22.00 g, 0.16 mol) according to the protocols as outlined in general procedure C to afford the title compound.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-fe058e4daa4d45f2a154f2724d90ec74
Source dataset
uspto-grants-2011_02
Patent number
US07884244B2

Reaction notes

Loading…