3-Methoxy-4-methoxycarbonylcinnamic acid → 3-(3-Methoxy-4-methoxycarbonylphenyl)propionic acid

HRID 369893Notes

Reaction equation

HRID 369893 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[C:14]([O:16][CH3:17])=[O:15])[CH:6]=[CH:7][C:8]([OH:10])=[O:9]>C(O)(=O)C.[C].[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])[CH:11]=[CH:12][C:13]=1[C:14]([O:16][CH3:17])=[O:15]

Participants

4

Reactant 1

HCID 543216923-Methoxy-4-methoxycarbonylcinnamic acid

Product 1

HCID 232825963-(3-Methoxy-4-methoxycarbonylphenyl)propionic acidYield 89.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

To a suspension of 3-methoxy-4-methoxycarbonylcinnamic acid (8.35 g) in acetic acid (200 ml) is added 10% palladium-carbon (1.0 g), and the mixture is subjected to hydrogenation at room temperature. The catalyst is removed by filtration, and the filtrate is concentrated under reduced pressure. The residue is crystallized from diethyl ether-n-hexane to give 3-(3-methoxy-4-methoxycarbonylphenyl)propionic acid (7.5 g).

Workup

  1. customis subjected to hydrogenation at room temperature
  2. customThe catalyst is removed by filtration
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. customThe residue is crystallized from diethyl ether-n-hexane

Sources & evidence

ORD record
ord-c7f664acf0934378873049caccf90656
Source dataset
uspto-grants-2000_10
Patent number
US06140330

Reaction notes

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