Methyl acetoacetate → 1-Hydroxybicyclo[3.3.1]nonan-3-one

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Reaction Steps

50.58 g of cyclohexenone and 72.95 g of methyl acetoacetate were measured and placed in a 1,000 ml flask. 300 ml of methanol was added to prepare the homogeneous solution. The solution was gradually mixed with 101.53 g of 28% sodium methoxide, and the mixture was refluxed in the flask equipped with a Dimroth condenser for 72 hours. The reaction solution was cooled, mixed with 100 ml of an aqueous solution containing 72.12 g of potassium hydroxide, and further refluxed for 13 hours. After the reaction was finished, the solvent was distilled away from the reaction solution under reduced pressure, and the residue was extracted with dichloromethane. The obtained organic layers were integrated, washed with a saturated aqueous solution of sodium chloride, and then dried over MgSO4. The solvent was distilled away under reduced pressure, and the residue was again dissolved in diethyl ether. The solution was reversibly extracted with water, and the obtained water layers were integrated and concentrated. The residue was recrystallized from diethyl ether to obtain the title compound as white crystals (41.19g, 50%).

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