Ethyl 4-(benzyloxy)-3-oxobutanoate → Ethyl 4-hydroxy-3-oxobutanoate

HRID 905113Notes

Reaction equation

HRID 905113 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][C:6]([CH2:8][O:9]CC1C=CC=CC=1)=[O:7])[CH3:2].[H][H]>[Pd]>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][C:6]([CH2:8][OH:9])=[O:7])[CH3:2]

Participants

4

Reactant 2

HCID 9813448Ethyl 4-(benzyloxy)-3-oxobutanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 13335342Ethyl 4-hydroxy-3-oxobutanoateYield 102%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

21.24 g of the 4-benzyloxyacetoacetic ethyl ester dissolved in acetic ester (100 ml) was inserted into a 200 ml steel autoclave provided with a magnetic stirrer and was hydrogenolized in the presence of 1.05 g Pd 5 percent on coal with hydrogen with a pressure of 5 atm. After the reaction was completed, which amounted to a period of about 2 hours, and after a 2 hour post-reaction time, the catalyst was filtered out. The filtrate was evaporated on a vacuum rotation evaporator at 35° C. The residue was dried in the high vacuum. 13.4 g of 4-hydroxyacetoacetic ethyl ester in the form of a slightly yellowish oil resulted.

Workup

  1. customprovided with a magnetic stirrer
  2. customafter a 2 hour post-reaction time
  3. filtrationthe catalyst was filtered out
  4. customThe filtrate was evaporated on a vacuum rotation evaporator at 35° C
  5. customThe residue was dried in the high vacuum

Sources & evidence

ORD record
ord-c6a45f03367b4b208717d4b7d06b7a69
Source dataset
uspto-grants-1983_12
Patent number
US04421922

Reaction notes

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