[C:1]([O:6][CH3:7])(=[O:5])[CH:2]([CH3:4])[OH:3].[CH2:8](O)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]C.[OH-].[Na+]>OS(O)(=O)=O.CO>[C:1]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])(=[O:5])[CH:2]([CH3:4])[OH:3]A 250 mL round bottom flask equipped with a spin bar and a distillation column was charged with 100 g (0.96 moles) of methyl lactate, 304.1 g (1.92 moles) of decyl alcohol, and 500 mg of H2SO4. The reaction was heated until methanol formation ceased. The reaction was then neutralized with 0.1N NaOH (100 mL) and extracted with ether. The organic layer was dried over MgSO4, filtered and dried in vacuo to give 400 g of crude mixture. The fractional distillation was carried out three times to give 98.5 g (45% yield, 100% pure by GC) of a clear colorless oil.
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