Benzoic acid, 4-(2-carboxyethenyl)-, methyl ester → 3-(4-(Methoxycarbonyl)phenyl)propanoic acid

HRID 369890Notes

Reaction equation

HRID 369890 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:15]=[CH:14][C:8]([CH:9]=[CH:10][C:11]([OH:13])=[O:12])=[CH:7][CH:6]=1)=[O:4]>C(O)(=O)C.[C].[Pd]>[CH3:1][O:2][C:3]([C:5]1[CH:15]=[CH:14][C:8]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:7][CH:6]=1)=[O:4]

Participants

4

Reactant 1

HCID 86881Benzoic acid, 4-(2-carboxyethenyl)-, methyl ester

Product 1

HCID 227166883-(4-(Methoxycarbonyl)phenyl)propanoic acidYield 82.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 4-methoxycarbonylcinnamic acid (4.64 g) in acetic acid (300 ml) is added 10% palladium-carbon (0.5 g), and the mixture is subjected to hydrogenation at 70° C. under atmospheric pressure for two hours. The catalyst is removed by filtration, and the filtrate is concentrated under reduced pressure. To the residue is added water, and the precipitated white powder is collected by filtration to give 3-(4-methoxycarbonylphenyl)propionic acid (3.87 g).

Workup

  1. customThe catalyst is removed by filtration
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. additionTo the residue is added water
  4. filtrationthe precipitated white powder is collected by filtration

Sources & evidence

ORD record
ord-275100d8ac6f4b45b012160d2001e4c8
Source dataset
uspto-grants-2000_10
Patent number
US06140330

Reaction notes

Loading…