Potassium Hydroxide → 5-Norbornene-2-carboxylic acid

Participants

Reaction Steps

27.5 g (110 mmol) of the Diels-Alder adduct obtained in the above step was dissolved in 420 ml of a mixture solvent of tetrahydrofuran-water (5:2), on ice cooling, 30.0 g (455 mmol) of potassium hydroxide (85%) in 120 ml of water was added, and the mixture was stirred at room temperature for 24 hours. After distilling off tetrahydrofuran, the residue was neutralized with 40 ml of concentrated hydrochloric acid, and the solution was extracted with a mixture solvent of hexane-methylene chloride (98:2) (150 ml×4). The extract was dried over anhydrous magnesium sulfate and filtered, the solvent was distilled off, and 15.7 g of crude 5-norbornene-2-carboxylic acid was obtained. Crude yield: 100%.

Provenance & Evidence