Tetrahydrofuran → cis-2-methyl-7-octadecene

Participants

Reaction Conditions

Reaction Steps

In a 1-liter reactor, a Grignard reagent was prepared from 5.0 g (0.206 mole) of magnesium and 46 g (0.2 mole) of 1-chloro-cis-3-tetradecene in exactly the same manner as in Example 4. Next, 100 g of tetrahydrofuran, 45.2 g (0.2 mole) of isoamyl p-toluenesulfonate and 0.5 g of cuprous iodide were placed in another 1-liter reactor and cooled to -20° C. Then, the above-described Grignard reagent was added dropwise thereto. After completion of the reaction, the mixture was stirred at 0° C. for 2 hours and then stirred without cooling until the temperature rose gradually to room temperature. Then, 100 g of a saturated aqueous ammonium chloride solution was added and the resulting mixture was allowed to separate into two layers. The organic layer was recovered and freed of solvent under reduced pressure. The resulting was distilled to obtain 16.1 g of 2-methyl-cis-7-octadecene (purity 96.0%, yield 62%, b.p. 155°-158° C./2 mmHg). MS(m/e): 56(100%), 266 (M+, 27%).

Provenance & Evidence