Benzyl 4-ethoxycarbonylmethoxybutyrate → 4-Ethoxycarbonylmethoxybutyric acid

HRID 487490Notes

Reaction equation

HRID 487490 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][O:7][CH2:8][CH2:9][CH2:10][C:11]([O:13]CC1C=CC=CC=1)=[O:12])=[O:5])[CH3:2]>O1CCCC1.[Pd]>[CH2:1]([O:3][C:4]([CH2:6][O:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 18991532Benzyl 4-ethoxycarbonylmethoxybutyrate

Product 1

HCID 223185004-Ethoxycarbonylmethoxybutyric acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

45 g (0.16 mol) of benzyl 4-ethoxycarbonylmethoxybutyrate 58 g are dissolved in 450 ml of tetrahydrofuran and the solution is hydrogenated under normal pressure at room temperature by addition of 4.5 g of 5% Pd/C. Upon cessation of hydrogenation, the catalyst is removed by filtration and the filtrate is concentrated by evaporation giving 4-ethoxycarbonylmethoxybutyric acid which is further reacted without purification.

Workup

  1. customUpon cessation of hydrogenation, the catalyst is removed by filtration
  2. concentrationthe filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-a7f5352e903e466fa5d39e2b328fab09
Source dataset
uspto-grants-1994_03
Patent number
US05294734

Reaction notes

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