Hydrochloric Acid → (3R)-3-benzoyloxy-tetradecanoyl chloride

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Reaction Steps

To a 20 L 3-neck round bottom flask equipped with a mechanical stirrer, nitrogen inlet, reflux condenser, heating mantle, vacuum system, and scrubber system for efficient removal of HCl and SO2 gases liberated during the reaction, is charged under nitrogen 15 moles of benzoic acid anhydride, 10 moles of concentrated anhydrous HCl in 4 L of THF, and 7.48 moles of the (3R)-3-hydroxy-tetradecanoic acid obtained from Example 1, above. The stirred mixture is placed under a N2 flow, which is vented to the scrubber system. The stirred mixture is heated to reflux for 3 hours during which the reaction becomes complete. The resulting solution is neutralized with 1N NaOH and the organic layer is separated from the aqueous layer. The aqueous layer is washed with THF and the resulting organic portions are combined, placed under vacuum and THF is removed. The resulting solid is dissolved in warm hexane, cooled and worked up to provide the product (3R)-3-benzoyloxy-tetradecanoyl chloride in about 95% yield.

Provenance & Evidence