Benzyl 3-(ethoxycarbonyl)-2-(2-methylpropyl)butenoate → 3-(Ethoxycarbonyl)-2-(2-methylpropyl)butanoic acid

HRID 1252383Notes

Reaction equation

HRID 1252383 reaction equation
[CH2:1]([O:3][C:4]([C:6]([CH3:22])=[C:7]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:8]([O:10]CC1C=CC=CC=1)=[O:9])=[O:5])[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4]([CH:6]([CH3:22])[CH:7]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:8]([OH:10])=[O:9])=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 53831566Benzyl 3-(ethoxycarbonyl)-2-(2-methylpropyl)butenoate

Product 1

HCID 199634113-(Ethoxycarbonyl)-2-(2-methylpropyl)butanoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

E and Z benzyl 3-(ethoxycarbonyl)-2-(2-methylpropyl)butenoate (5.0 g.) was hydrogenated at 120 psi at 60° C. in methanol (50 mls.) in the presence of 10% palladium on charcoal (0.25 g.) for 48 hours. The resultant mixture was filtered through Celite and the solvent removed by evaporation in vacuo to yield 3-(ethoxycarbonyl)-2-(2-methylpropyl)butanoic 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-46370259377646a6836d117800836d9a
Source dataset
uspto-grants-1988_05
Patent number
US04743587

Reaction notes

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