Hydrochloric Acid → 2,2-dimethyl-3-oxocyclobutanecarboxylic acid

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Reaction Conditions

Reaction Steps

To a solution of methyl 2,2-dimethyl-3-oxocyclobutanecarboxylate (1.0 equiv.) in MeOH (1.1 M) was added aqueous solution of sodium hydroxide (4.48 N, 2.0 equiv.), and the resulting mixture was stirred at 50° C. for 2 h. The starting material was consumed as monitored by thin layer chromatography, eluting with 20% ethyl acetate in petroleum ether. After removal of the volatile solvent, aqueous solution of hydrochloride (2 N, 1.4 equiv.) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under vacuum to afford the product (88% yield) as a white solid, which was used for the next step without further purification. 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