7,8-Epoxy-6-oxo-octanoic acid methyl ester → 8-Hydroxy-6-oxo-octanoic acid methyl ester
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
Product 1
Reagents, catalysts & solvents 2
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.