3,5-Dichlorocinnamic acid → 3-(3,5-Dichlorophenyl)propionic acid

HRID 890759Notes

Reaction equation

HRID 890759 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]([OH:13])=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1>C1COCC1.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 1

HCID 1765043,5-Dichlorocinnamic acid

Product 1

HCID 8193053-(3,5-Dichlorophenyl)propionic acidYield 97.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 10% Pd/C (1.5 g) in THF (200 mL) was added 3-(3,5-dichlorophenyl)-acrylic acid (11.5 g). The reaction was hydrogenated on a Parr shaker at 50 psi for 3 h. The catalyst was removed by filtration through celite and the organic solution was concentrated in vacuo to afford 3-(3,5-dichlorophenyl)-propionic acid (11.3 g). 1H NMR (400 MHz, CDCl3) δ 7.00–7.35 (m, 3H), 2.89 (t, 2H), 2.66 (t, 2H).

Workup

  1. customThe catalyst was removed by filtration through celite
  2. concentrationthe organic solution was concentrated in vacuo

Sources & evidence

ORD record
ord-ebed3be1e99844ffbec4e7d7707689b8
Source dataset
uspto-grants-2006_02
Patent number
US06998423B2

Reaction notes

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