Potassium Hydroxide → 4-(Methoxy)-1-methyl-2,6,7-trioxabicyclo[2.2.2]octane

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Powdered potassium hydroxide (16.2 g, 0.290 mol) is suspended in 100 mL of dimethyl sulfoxide and the mixture is stirred at 25° C. for 5 min. Then 4-(hydroxymethyl)-1-methyl-2,6,7-trioxabicyclo[2.2.21octane (10.0 g, 0.062 mol) is added followed by bromomethyl methyl ether (9.3 g, 6.1 mL, 0.074 mol). The reaction mixture is stirred for 30 min and then diluted with water (1 L) and extracted with dichloromethane several times. The combined organic layers are washed with saturated sodium chloride (100 mL), dried over anhydrous sodium sulfate and evaporated under reduced pressure to give 4-(methoxy)-1-methyl-2,6,7-trioxabicyclo[2.2.2]octane. This crude material is dissolved in methanol (100 mL) and stirred with pyridinium p-toluenesulfonate (1.6 g, 6.200 mmol) in water (100 mL) for 30 min. The pH of the solution is adjusted to 7 with solid sodium bicarbonate and the solvents are removed under reduced pressure. The resulting solids are triturated with methanol and the methanol solution is evaporated to give 2-(methoxymethoxy)-1,1,1-tris(hydroxymethyl)ethane.

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