Sodium Hydroxide → 1-[[(2-Furanylmethoxy)carbonyl]amino]cyclohexanecarboxylic acid

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Reaction Steps

28.13 g (0.1 mol) of 1-[[(2-furanylmethoxy)carbonyl]amino]cyclohexanecarboxylic acid methyl ester was added to a mixture solution of 150 ml of 2N aqueous sodium hydroxide solution and 200 ml of tetrahydrofuran, and the mixture was heated under reflux for 18 hours. After the solvent was distilled off, water was added to the residue, and the mixture was washed with diethyl ether. After potassium hydrogensulfate was added to the aqueous layer to acidify it, it was extracted with ethyl acetate twice. After the organic layer was washed with saturated brine and it was dried with anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. Diisopropyl ether was added to the residue, and the mixture was stirred for 18 hours. The obtained crystal was collected by filtration to obtain 19.89 g (74%) of the title compound.

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