3-(3-Chloro-2,4-dimethoxyphenyl)prop-2-enoic acid → 3-(3-Chloro-2,4-dimethoxyphenyl)propionic acid

HRID 488546Notes

Reaction equation

HRID 488546 reaction equation
[Cl:1][C:2]1[C:3]([O:15][CH3:16])=[C:4]([CH:10]=[CH:11][C:12]([OH:14])=[O:13])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]>CO.C1COCC1.[Pd]>[Cl:1][C:2]1[C:3]([O:15][CH3:16])=[C:4]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

5

Reactant 1

HCID 688767863-(3-Chloro-2,4-dimethoxyphenyl)prop-2-enoic acid

Product 1

HCID 219461123-(3-Chloro-2,4-dimethoxyphenyl)propionic acidYield 99%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 3a (12.57 g, 51.88 mmol) in a mixture of MeOH (50 ml) and THF (200 ml) was hydrogenated at 50 psi in the presence of 10% Pd/C (0.3 g) for 4 h. The catalyst was removed by filtration through Celite and the filtrate was concentrated to afford 12.6 g (51.5 mmol, 99% yield) of analytically pure (HPLC, 1H NMR) 4a as a white solid. 1H NMR (DMSO-d6): δ 7.15 (d, J=8.6 Hz, 1H), 6.86 (d, J=8.6 Hz, 1H), 3.81 (s, 3H), 3.75 (s, 3H), 2.78 (t, J=7.5 Hz, 2H), 2.49 (t, J=7.5 Hz, 2H).

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-70cacae8a812446481068553b4181730
Source dataset
uspto-grants-2005_12
Patent number
US06972339B2

Reaction notes

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