7,8-Epoxy-6-oxo-octanoic acid methyl ester → 8-Hydroxy-6-oxo-octanoic acid methyl ester

HRID 1063476Notes

Reaction equation

HRID 1063476 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:12])[CH:9]1[O:11][CH2:10]1>[Pt](=O)=O.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:12])[CH2:9][CH2:10][OH:11]

Participants

4

Reactant 1

HCID 179590927,8-Epoxy-6-oxo-octanoic acid methyl ester

Product 1

HCID 120390238-Hydroxy-6-oxo-octanoic acid methyl esterYield 67%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A 100 ml autoclave was charged under argon with 9.4 g (50 mmol) of 7,8-epoxy-6-oxo-octanoic acid methyl ester, with 0.4 g of platinum(IV) oxide catalyst, and with 50 ml of ethyl acetate. The hydrogenation was carried out for 16 hours at 20° C., at a constant pressure of 50 bar pure H2 and with intensive stirring. When the reaction was complete, the catalyst was filtered off and the solvent was distilled off using a rotary evaporator. Purification of the residue by column chromatography (silica gel, ethyl acetate/n-hexane) yielded 6.3 g (67%) of 8-hydroxy-6-oxo-octanoic acid methyl ester.

Workup

  1. filtrationthe catalyst was filtered off
  2. distillationthe solvent was distilled off
  3. customa rotary evaporator
  4. customPurification of the residue by column chromatography (silica gel, ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-66e7b5b3cd42496da975bdcdbf282587
Source dataset
uspto-grants-2005_11
Patent number
US06965029B2

Reaction notes

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