Sodium Azide → 12-Azido-1-dodecanol

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A mixture of 12-bromo-1-dodecanol (246 mg, 0.927 mmol) in t-butanol (1.8 mL, 0.5 M) was treated with sodium azide (121 mg, 1.855 mmol, 2 eq), tetrabutylammonium iodide (17 mg, 0.0464 mmol, 0.05 eq) and sat. aq. sodium bicarbonate solution (0.9 mL) in that order. The mixture was stirred at room temperature for 4 days. The mixture was filtered through a plug of celite and the cake rinsed with ethyl acetate (20 mL). The combined filtrate and washings were evaporated onto silica gel and purified by flash column (2.5×18 cm, gradient elution with hexane-ethyl acetate 6:1, 4:1 to 2:1) to give 12-Azido-1-dodecanol as a colourless oil (193 mg, 92%). 1H NMR (CDCl3, 400 MHz): 3.62 (t, 2H, J=7.0, OCH2), 3.24 (t, 2H, J=7.0, NCH2), 1.61-1.51 (m, 4H), 1.35-1.25 (m, 16H).

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