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, the mixture was extracted with ethyl acetate twice. After the organic layer was washed with saturated brine, it was dried with anhydrous magnesium sulfate, and thereafter 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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