3-(2-Chlorophenyl)acrylic acid → 3-(2-Chlorophenyl)propanoic acid

HRID 1363671Notes

Reaction equation

HRID 1363671 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[CH:9][C:10]([OH:12])=[O:11]>C1COCC1.[Rh]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]([OH:12])=[O:11]

Participants

4

Reactant 1

HCID 195673-(2-Chlorophenyl)acrylic acid

Product 1

HCID 956763-(2-Chlorophenyl)propanoic acid

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3-(2-chloro-phenyl)-acrylic acid (10.00 g, 55.00 mmol) in THF was mixed with Rh/Al2O3 (500 mg) and hydrogenated for 14 hours. The reaction mixture was filtered through celite and the filtrate was concentrated to give 3-(2-chloro-phenyl)-propionic acid. 3-(2-chloro-phenyl)-propionic acid (10.0 g, 43.70 mmol) was then reacted with SOCl2 (6.00 mL, 82.26 mmol) and AlCl3 (8.00 g, 60.00 mmol) according to the protocols as outlined in general procedure C to afford the title chloroindanone. iv Berrier, C.; Gesson, J. P.; Jacquesy, J. C.; Renoux, A. Tetrahedron 1984, 40, 4973-4980.

Workup

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

Sources & evidence

ORD record
ord-ba16a2d19c9548d9818cd7b64ea616dd
Source dataset
uspto-grants-2011_02
Patent number
US07884244B2

Reaction notes

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