Hydrochloric Acid → 4-Oxo-2-adamantyl chloromethyl ether

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A separable flask having a volume of one liter equipped with a nozzle for introducing hydrogen chloride gas was equipped with a stirring device and charged with 50.0 g (301 mmol) of 4-oxo-2-adamantanol, 13.6 g (450 mmol) of paraformaldehyde, 36.2 g (300 mmol) of magnesium sulfate and 650 ml of dried dichloromethane, and it was cooled to 0° C. on an ice bath and stirred. Hydrogen chloride gas generated by mixing 300.7 g (5 mole) of sodium chloride with 700 ml of conc. sulfuric acid was blown thereinto through the nozzle for one hour. After further stirring for 3 hours, magnesium sulfate was filtered, and then the solution was analyzed by gas chromatography to confirm that 4-oxo-2-adamantanol was completely converted and that the intended product was obtained at a selectivity of 93.2%. Hydrogen chloride and dichloromethane were removed, and then refining was carried out by distillation to isolate 55.0 g (256 mmol, yield 85.2%, GC purity 98.8%) of the intended product.

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