Iodine → 5,9-Dimethylpentadecane

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Magnesium (0.54 g, 22.2 mmol) is etched with iodine and 0.5 ml of a solution of 93% 1-chloro-2,6-dimethyldecane (4.5 g, 20.7 mmol) in tetrahydrofuran (4 ml) is added at 60° C. After the reaction has been started by addition of a drop of 1,2-dibromoethane the rest of the solution is added dropwise. The mixture is diluted with tetrahydrofuran (4 ml) and stirred under reflux for 2.5 h, then cooled to -20° C. 1-Bromopentane (3.8 g, 25 mmol) in tetrahydrofurane (4 ml) and 0.5M dilithium tetrachlorocuprate in tetrahydrofuran (3 ml) are added, and the mixture is stirred at -20° C. for 2 h, at 0° C. for 2 h, and at room temperature overnight. Subsequent treatment with ammonium chloride solution and distillation gives 3.22 g of 5,9-dimethylpentadecane, a yield of 64.8% based on the amount of C12 -alkyl chloride.

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