Benzyl 5-(3-ethoxy-2-ethoxy-3-oxo-1-propenyl)-2-methoxybenzoate → 5-(3-Ethoxy-2-ethoxy-3-oxopropyl)-2-methoxybenzoic acid

HRID 1816552Notes

Reaction equation

HRID 1816552 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[C:5]([O:25][CH2:26][CH3:27])=[CH:6][C:7]1[CH:8]=[CH:9][C:10]([O:23][CH3:24])=[C:11]([CH:22]=1)[C:12]([O:14]CC1C=CC=CC=1)=[O:13])[CH3:2].[H][H]>C(O)C.[C].[Pd]>[CH2:1]([O:3][C:4](=[O:28])[CH:5]([O:25][CH2:26][CH3:27])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:23][CH3:24])=[C:11]([CH:22]=1)[C:12]([OH:14])=[O:13])[CH3:2]

Participants

5

Reactant 2

HCID 69803661Benzyl 5-(3-ethoxy-2-ethoxy-3-oxo-1-propenyl)-2-methoxybenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 109134625-(3-Ethoxy-2-ethoxy-3-oxopropyl)-2-methoxybenzoic acidYield 97.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

1.6 g of benzyl 5-(3-ethoxy-2-ethoxy-3-oxo-1-propenyl)-2-methoxybenzoate was dissolved in 30 ml ethanol, 0.35 g of 10% palladium-carbon was added, and the mixture was stirred for 16 hours in a hydrogen atmosphere. The catalyst was filtered through Celite and the solvent was evaporated. Then, the residue was subjected to silica gel column chromatography, and from fractions eluted with hexane-ethyl acetate (2:1), 1.2 g of 5-(3-ethoxy-2-ethoxy-3-oxopropyl)-2-methoxybenzoic acid was obtained.

Workup

  1. filtrationThe catalyst was filtered through Celite
  2. customthe solvent was evaporated
  3. washfrom fractions eluted with hexane-ethyl acetate (2:1)

Sources & evidence

ORD record
ord-6cb216efd32d4767829c99d81ef4121c
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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