Benzyl 3-(ethoxycarbonyl)-2-(2-methylpropyl)propenoate → 3-(Ethoxycarbonyl)-2-(2-methylpropyl)propanoic acid

HRID 745617Notes

Reaction equation

HRID 745617 reaction equation
[CH2:1]([O:3][C:4]([CH:6]=[C:7]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:8]([O:10]CC1C=CC=CC=1)=[O:9])=[O:5])[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4]([CH2:6][CH:7]([CH2:18][CH:19]([CH3:20])[CH3:21])[C:8]([OH:10])=[O:9])=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 53921709Benzyl 3-(ethoxycarbonyl)-2-(2-methylpropyl)propenoate

Product 1

HCID 143030363-(Ethoxycarbonyl)-2-(2-methylpropyl)propanoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

E and Z benzyl 3-(ethoxycarbonyl)-2-(2-methylpropyl)propenoate (25.0 g., 0.09 mol.) was dissolved in ethanol and hydrogenated at 50° C. under 37.5 psi in the presence of 5% palladium on charcoal (2.5 g). The resultant mixture was filtered through Celite and the solvent removed by evaporation in vacuo to yield 3-(ethoxycarbonyl)-2-(2-methylpropyl)propanoic acid as a mixture of isomers in the form of a thick oil.

Workup

  1. filtrationThe resultant mixture was filtered through Celite
  2. customthe solvent removed by evaporation in vacuo

Sources & evidence

ORD record
ord-c7e2758ac4be4f428acc132326682abb
Source dataset
uspto-grants-1986_07
Patent number
US04599361

Reaction notes

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