Diethyl Ether → 1,3-Diacetoxymethyl-5-[2-[1-(formylmethyl)cyclohexyl]ethoxy]benzene

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Reaction Steps

To a solution of 2-[1-[2-(3,5-diacetoxymethylphenyoxy)ethyl]cyclohexyl]ethanol (synthesized in Example 31) (430 mg) dissolved in dichloromethane (5 mL) were added diacetic acid iodobenzene (388 mg) and 2,2,6,6-tetramethyl-1-piperidinyloxy free radical (18.5 mg) successively at room temperature. The solution was stirred for 15 hours. Diethyl ether was added to the solution and it was washed in turn with a 10% aqueous sodium thiosulfate solution, 1N hydrochloric acid, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate, and filtered. The filtrate was then concentrated under reduced pressure to give the title compound (479 mg). This product was subjected to the subsequent step without further purification.

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