- Synthesis of 11-Hydroxyundecanoic lactone
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11-Hydroxyundecanoic lactone (CAS NO.: ), which is also known as , could be produced through the following synthetic route.
A 1-l., three-necked, round-bottomed flask equipped with an internal thermometer, mechanical stirrer, dropping funnel, and calcium chloride drying tube is charged with 500 ml. of dimethyl sulfoxide and 15 g. (0.11 mole) of potassium carbonate. The mixture is heated to 100°, and a solution of 10.0 g. (0.0377 mole) of 11-bromoundecanoic acid in 200 ml. of dimethyl sulfoxide is added dropwise with vigorous stirring over 1 hour. After cooling at room temperature, the mixture is decanted and filtered free of any suspended solid material through a Büchner funnel with occasional suction. The solid residue is rinsed with 50 ml. of dimethyl sulfoxide, and the washings are added to the original filtrate. The resulting clear solution is diluted with 250 ml. of water and extracted with three 250-ml. portions of petroleum ether. The combined organic layers are washed with 200 ml. of water, dried over anhydrous sodium sulfate, and concentrated, leaving ca. 7 g. of crude material. Simple distillation at reduced pressure from a small Claisen flask yields 5.5–5.8 g. (79–83%) of pure 11-hydroxyundecanoic lactone as a colorless, musk-smelling liquid, b.p. 124–126° (13 mm.), nD19 1.4721. The residue is ground with 5 ml. of hexane and filtered, affording 0.4–0.7 g. (6–10%) of the 24-membered dilactone 1,13-dioxacyclotetracosane-2,14-dione as white crystals, m.p. 71.5–72° (from hexane).
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