Potassium Hydroxide → 4-[2-(Ethylsulfonyl)ethyl]bicyclo[2.2.2]octane-1-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

Ester 1-3 (880 mg, 3 mmol) was dissolved in 10% water/methanol solution (100 mL) and treated with 1 g of potassium hydroxide. The reaction was heated at 60° C. for 1 h then at 45° C. overnight. The mixture was concentrated in vacuo then acidified to pH 2 with 1M HCl and extracted with three portions of methylene chloride. The organic layers were combined, dried over anhydrous sodium sulfate and evaporated to give 4-[2-(ethylsulfonyl)ethyl]bicyclo[2.2.2]octane-1-carboxylic acid (1-4) (810 mg).

Provenance & Evidence