3,5-Dichlorocinnamic acid → 3-(3,5-Dichlorophenyl)propionic acid
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]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
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
- customThe catalyst was removed by filtration through celite
- concentrationthe organic solution was concentrated in vacuo
Sources & evidence
- ORD record
- ord-3611b7084aea452f8a83e00624da6526
- Source dataset
- uspto-grants-2003_11
- Patent number
- US06649657B2
Reaction notes
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