[OH:1][C@@H:2]([CH3:8])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[CH2:9]([OH:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4]>[OH:1][C@@H:2]([CH3:8])[CH2:3][C:4]([O:6][CH2:7][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:5].[CH2:9]([OH:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1A chemical reference for desired product was prepared as follows. Methyl (S)-(+)-3-hydroxybutyrate (Aldrich) was dissolved in benzyl alcohol and treated with a catalytic amount of titanium tetraisopropoxide. The mixture was aged at 60° C. for 24 hours. Partial concentration on a rotary evaporator and filtration afforded benzyl (S)-(+)-3-hydroxybutyrate and residual benzyl alcohol.
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