The general procedure for the synthesis of cis-4-hydroxycyclohexanecarboxylic acid from methyl cis-4-hydroxycyclohexanecarboxylate was as follows: 20 g of methyl cis-4-hydroxycyclohexanecarboxylate was dissolved in 80 mL of methanol and cooled in an ice water bath. A 5 mol/L sodium hydroxide solution of 40 mL was slowly added, and after the drop was completed, the reaction mixture was stirred at room temperature overnight. After the reaction was completed, 150 mL of water was added to dilute it. The mixture was extracted twice with ethyl acetate and the organic phase was discarded. The aqueous phase was adjusted to pH 3 with 1 mol/L HCl and extracted twice with 50 mL of ethyl acetate to combine the organic phases. The organic phase was washed twice with saturated saline in turn, dried and decolorized. After filtration, the ethyl acetate was concentrated under reduced pressure to recover the ethyl acetate, and 16 g of white solid product was obtained in 90% yield.
