4-Carbethoxycinnamic acid → 4-Ethoxycarbonylbenzenepropanoic acid
Reaction equation
[C:1]([C:6]1[CH:16]=[CH:15][C:9]([CH:10]=[CH:11][C:12]([OH:14])=[O:13])=[CH:8][CH:7]=1)([O:3][CH2:4][CH3:5])=[O:2]>CCO.[Rh]>[CH2:4]([O:3][C:1]([C:6]1[CH:16]=[CH:15][C:9]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:8][CH:7]=1)=[O:2])[CH3:5]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 4-carbethoxycinnamic acid (4.9 g) in EtOH (120 ml) was hydrogenated over 5% Rh/C (485 mg) at atmospheric pressure for 21 hr. The solution filtered and stripped. The residue was crystallized from cyclohexane to afford 2.23 g (46%) of the title compound as white crystals; mp 108.5°-110.5°.
Workup
- filtrationThe solution filtered
- customThe residue was crystallized from cyclohexane
Sources & evidence
- ORD record
- ord-5c92a31500f442ccacf5c8bb99184d6e
- Source dataset
- uspto-grants-1995_05
- Patent number
- US05414132
Reaction notes
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