Methanol → E-5-Decen-1-ol

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A portion of the 5-decenyl acetate can be removed and converted to the corresponding alcohol according to the following procedure and the scale can be adjusted as necessary. 15.0 g (67 mmol) of the 5-decenyl acetate, 35 mL of methanol and 34 mL of 2 M sodium hydroxide are added to a 250 mL round-bottomed flask. This mixture is stirred for three hours at room temperature. After three hours the hydrolysis is complete, 10 mL of hexane is then added and the solution is washed with 10 mL of 1 M HCl, 10 mL of NaHCO3-saturated water and 10 mL of brine. The organic phase is dried with sodium sulfate and filtered, and the hexane is removed under reduced pressure to yield 9.4 g of 5-decenol. GC analysis shows the isometric ratio of the 5-decenol to be conserved.

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