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Properties of substance:

3-oxocyclobutane-1-carboxylic acid

Synonyms:

3-oxocyclobutanecarboxylic acid
3-ketocyclobutanecarboxylic acid

Group of substances:

organic

Physical appearance:

colorless needles crystals

Empirical formula (Hill's system for organic substances):

C5H6O3

Structural formula as text:

OC(CH2)2CHCOOH

Melting point (°C):

69-70

Synthesis 1:

Reference: Pigou, P. E., & Schiesser, C. H. Convenient route to 1,3-disubstituted cyclobutanes. An inexpensive synthesis of 3-oxocyclobutanecarboxylic acid / Journal of Organic Chemistry. - 1988. - Vol. 53, No. 16 pp. 3843 [doi: 10.1021/jo00251a033]

Diisopropyl 3,3-dimethoxycyclobutane-1,1-dicarboxylate (287.5 g, 1.0 mol) was stirred with 20% hydrochloric acid (750 mL) at reflux for 60 h.

After cooling, the solution was continuously extracted with ether for 18 h. The ether was removed at reduced pressure, leaving a yellow oil, which crystallized on standing and proved to be the title acid (111 g, 97%), which was characterized by conversion to its ethyl ester, whose physical properties were in accord with literature data: 1H NMR (CCl4) ? 4.17 (2 H, q, J = 7 Hz), 3.27 (5 H, m), 1.27 (3 H, t, J = 7 Hz); 13C NMR (CCl4) 201.48 (C3), 173.21 (CO2), 60.57 (OCH2), 51.20 (C2 and C4), 27.09 (C1), 14.09 (CH3).

References:

  1. Caserio, F. F., & Roberts, J. D. Small-ring Compounds. XXI. 3-Methylenecyclobutanone and Related Compounds / Journal of the American Chemical Society. - 1958. - Vol. 80, No. 21. - pp. 5838 [DOI: 10.1021/ja01554a064]

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    © Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru