1-Iodooctadecane → Tetraoctadecylammonium iodide

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Tetraoctadecylammonium iodide is prepared according to the following process. 70 mg (0.090 mmol) trioctadecylamine, 0.10 g (0.26 mmol) octadecyl iodide (recrystallized from 95% material, Fluka), and 3 ml CH3CN (HPLC grade, Fisher) are placed into a 10 ml roundbottomed flask. The mixture is refluxed under a dry nitrogen atmosphere with stirring for 5 days. 55 mg (53%) white solid, mp 104°-105° C., is recovered after the solvent is evaporated, and recrystallized twice in ethanol/Et2O. IR(KBr) 2918, 2855 (C-H stretching, vvs), 1471, 1386(C-H bending, w) cm-1. 1HNMR(CDCl3) δ 3.48-3.16(CH2, m, 8H), 1.78-0.81 (heptadecyl groups, m, 148H).

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