Sodium Hydroxide → 2,2-dimethyl-3-oxocyclobutanecarboxylic acid

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Reaction Conditions

Reaction Steps

To a solution of methyl 2,2-dimethyl-3-oxocyclobutanecarboxylate (5.0 g, 32.1 mmol) in MeOH (37.5 mL) was added an aqueous solution of sodium hydroxide (4.48 N, 18.5 mL, 84 mmol). The resulting mixture was stirred at 50° C. for 2 h. After completion, the excess MeOH was removed under reduced pressure and the mixture was extracted with diethyl ether (15 mL). The aqueous solution was neutralized with hydrochloric acid (4 N, 30 mL) and the mixture was extracted with ethyl acetate (100 mL×2). The combined organic layers were washed with brine (15 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under vacuum to afford the title product (3.9 g, 27.5 mmol, 86% yield) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ (ppm) 12.4 (br, 1H), 3.31-3.23 (m, 1H), 3.17-3.08 (m, 1H), 2.97-2.91 (m, 1H), 1.22 (s, 3H), 1.04 (s, 3H).

Provenance & Evidence