2-Propenoic acid, 3-(4-chlorophenyl)- → beta-(p-Chlorophenyl)propionic acid

HRID 1363674Notes

Reaction equation

HRID 1363674 reaction equation
[Cl: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]>[Cl: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 153712-Propenoic acid, 3-(4-chlorophenyl)-

Product 1

HCID 123137beta-(p-Chlorophenyl)propionic acid

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3-(4-Chloro-phenyl)-acrylic acid (25.00 g, 0.14 mol) 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-chloro-phenyl)-propionic acid. 3-(4-chloro-phenyl)-propionic acid was then reacted with SOCl2 (15.00 mL, 0.21 mol) and AlCl3 (20.20 g, 0.15 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-782d43610efa4130b36a91c8670f3cd1
Source dataset
uspto-grants-2011_02
Patent number
US07884244B2

Reaction notes

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