Ethyl 3-(2-isobutoxyphenyl)-2-propenoate → Ethyl 3-(2-isobutoxyphenyl)propanoate

HRID 2249672Notes

Reaction equation

HRID 2249672 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:12]=[CH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:2]([CH3:4])[CH3:3].[H][H]>C(O)C.[C].[Pd]>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 68983960Ethyl 3-(2-isobutoxyphenyl)-2-propenoateHCID 178418361HCID 178418361, compound

Product 1

HCID 17816468Ethyl 3-(2-isobutoxyphenyl)propanoateYield 50.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

In 15 ml of ethanol is dissolved 1.50 g of ethyl 3-(2-isobutoxyphenyl)-2-propenoate, to which is added 0.30 g of 5% palladium-carbon. The mixture is stirred at ambient temperature for one hour in a stream of hydrogen. The reaction mixture is filtered with Celite, and the solvent is distilled off from the filtrate under reduced pressure. The residue thus obtained is purified by silica gel column chromatography to obtain 0.76 g of ethyl 3-(2-isobutoxyphenyl)propionate as a colorless oily product.

Workup

  1. filtrationThe reaction mixture is filtered with Celite
  2. distillationthe solvent is distilled off from the filtrate under reduced pressure
  3. customThe residue thus obtained
  4. customis purified by silica gel column chromatography

Sources & evidence

ORD record
ord-62d0fe9896714874b1398273507f4d4e
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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