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

Participants

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. After reaction completion, the excess MeOH was removed under reduced pressure, and the mixture was extracted with diethyl ether, then the aqueous solution was neutralized with hydrochloride acid (4 N, 2.9 equiv.). The mixture was extracted with ethyl acetate, the organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under vacuum to afford the title product (88% yield) as 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