Methanol → 5-Chloro-2-cyclohexyl-valeric acid

Participants

Reaction Conditions

Reaction Steps

A 5 N sodium hydroxide solution (2.5 ml) was added to a solution of methyl 5-chloro-2-cyclohexyl-valerate (1.00 g) in THF (3 ml)-methanol (6 ml). The reaction solution was stirred at room temperature for six hours and at 60° C. for further two hours. After allowing the reaction solution to cool, water and diethyl ether were added to the reaction solution, and the aqueous layer was separated. 5 N hydrochloric acid (2.6 ml) and ethyl acetate were added to the aqueous layer, and the organic layer was separated. The ethyl acetate extraction layer was washed with brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (heptane-ethyl acetate system) to obtain 5-chloro-2-cyclohexyl-valeric acid (287 mg).

Provenance & Evidence