4-Carbethoxycinnamic acid → 4-Ethoxycarbonylbenzenepropanoic acid

HRID 1165529Notes

Reaction equation

HRID 1165529 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

HCID 542204274-Carbethoxycinnamic acid

Product 1

HCID 218216904-Ethoxycarbonylbenzenepropanoic acidYield 46%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 702EthanolSolvent

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 was 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

  1. filtrationThe solution was filtered
  2. customThe residue was crystallized from cyclohexane

Sources & evidence

ORD record
ord-914c565aeb654e6faac0adf5866a2542
Source dataset
uspto-grants-1990_03
Patent number
US04910190

Reaction notes

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