Sodium Iodide → Methyl 11-iodoundecanoate

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Reaction Steps

11-Bromo undecanoic acid methyl ester (20.2 g, 72.3 mmol) was dissolved in acetone (200 ml). Sodium iodide (54 g, 361 mmol) was added and reaction was refluxed under nitrogen for 16 h. After cooling to rt the salts were filtered off. The filtrate was concentrated under vacuum and water (200 ml) was added. The solution was extracted with AcOEt (2×100 ml) adding some sat. NaCl to aid phase separation. The organic extracts were pooled and washed with water (100 ml) plus a little sat. NaCl, and sat. NaCl (50 ml). Dry over MgSO4. The solution was a red-orange color. Three teaspoons of activated charcoal were added. After mixing, the solution was filtered through a bed of celite. The filtrate was concentrated under vacuum to yield a light yellow oil (20.96 g, 89%).

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