Benzyl 4-acetoxypentanoate → 4-Acetoxypentanoic acid

HRID 376165Notes

Reaction equation

HRID 376165 reaction equation
[C:1]([O:4][CH:5]([CH3:18])[CH2:6][CH2:7][C:8]([O:10]CC1C=CC=CC=1)=[O:9])(=[O:3])[CH3:2]>[Pd].C(O)C>[C:1]([O:4][CH:5]([CH3:18])[CH2:6][CH2:7][C:8]([OH:10])=[O:9])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 18991525Benzyl 4-acetoxypentanoate

Product 1

HCID 147371984-Acetoxypentanoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

87.5 g (0.35 mol) of benzyl 4-acetoxypentanoate are dissolved in 900 ml of abs. ethanol and the solution is hydrogenated at room temperature under normal pressure with the addition of 5 g of 10% Pd/C as catalyst. Upon cessation of hydrogenation, the catalyst is removed by filtration and the filtrate is concentrated by evaporation. Distillation of the residue gives 4-acetoxypentanoic acid as a colourless oil of b.p. 110°-112° C./2.10-2 torr.

Workup

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

Sources & evidence

ORD record
ord-92d4e274b4614ac78b7dfd3697c25a4d
Source dataset
uspto-grants-1996_01
Patent number
US05488140

Reaction notes

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