Pyridine → 11-Chloro-1-undecene

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A 1-liter, 3-neck flask equipped with a mechanical stirrer, reflux condenser, argon inlet and addition funnel was placed in an oil bath at 50° C. To the flask was added methylene chloride (400 milliliters), undecylenol (100 grams) and then pyridine (55.7 grams). Thionyl chloride (78.9 grams) in methylene chloride (100 milliliters) was added dropwise under reflux over 5 hours. The mixture was filtered, the solvent was removed from the filtrate using a rotary evaporator, and the resultant oil was refiltered and then distilled using a column packed with glass Raschig rings to yield two distillate portions. The fraction collected between 100° C. and 110° C. at 1 millimeter of mercury was retained and redistiiled using a Kugelrohr apparatus available from Aldrich. The yield of undecylenyl chloride was 40 grams of oil collected between 80° C. and 85° C. at 1 millimeter of mercury, which was identified using 13C NMR spectrometry.

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