Sodium Hydroxide → Bicyclo[2.2.2]octane-2-carboxylic acid

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Reaction Steps

Sodium hydroxide (2.5N, 22.4 mL, 56 mmol) was added to a methanolic solution of methyl bicyclo[2.2.2]octane-2-carboxylate (4.7 g, 28 mmol in 50 mL) at ambient temperature and the mixture was stirred for 16 hours. The solvent was concentrated in vacuo, water added (20 mL) and the solution made acidic with IN aqueous HCl. The product was extracted into dichloromethane (3×50 mL), the combined organic layers washed with water (25 mL), dried over anhydrous magnesium sulfate, filtered and concentrated on a rotary evaporator to afford the titled compound of formula (III) as a white solid (4.3 g, 100% yield).

Provenance & Evidence