Sodium Hydroxide → 1-(Methoxycarbonyl)cyclopropane-1-carboxylic acid

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Reaction Conditions

Reaction Steps

Dimethyl cyclopropane-1,1-dicarboxylate (26.08 mL, 189.87 mmol) is dissolved in methanol (319 mL) and the solution is cooled to 0° C. 1 N NaOH (190 mL, 190 mmol, 1 eq) in water is added dropwise. The resulting mixture is stirred at RT overnight. The solution is concentrated under reduced pressure to remove the methanol and the resulting aqueous solution is washed with dichloromethane (3×50 mL) and acidified with 1 N HCl (pH=2-3). The solution is then extracted with ethyl acetate (5×100 mL) and dichloromethane (3×50 mL). The combined organic portions are dried over MgSO4, filtered, and concentrated to afford the title compound (16.4 g, 60%). 1H NMR (400 MHz, CDCl3); δ 1.9-1.7 (m, 4H), 3.78 (s, 3H).

Provenance & Evidence