Hydrochloric Acid → 2,2,3,3-Tetrafluoro-1-Hydroxy-4-n-Propylbicyclo[2.2.2]octane

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Reaction Conditions

Reaction Steps

A mixture of 2,2,3,3-tetrafluoro-1-pentylcarbonyloxy-4-n-propylbicyclo[2.2.2]octane (11) (0.30 g), potassium hydroxide (0.10 g), water (0.5 mL), and ethanol (2.0 mL) was stirred at 70° C. for 20 minutes. The mixture was neutralized with hydrochloric acid, added with ethyl acetate (30 mL), and the organic layer was washed with aqueous sodium hydrogen carbonate solution. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was then vaporized off under reduced pressure, to thereby obtain a crude product. The crude product was purified by silica gel column chromatography (hexane/ethyl acetate=3:1), to thereby obtain 2,2,3,3-tetrafluoro-1-hydroxy-4-n-propylbicyclo[2.2.2]octane (12) (yield=0.20 g, yield ratio=94%) as a colorless clear solid.

Provenance & Evidence