I. R. Knyazeva, N. P. Romashov, V. V. Syakaev, D. P. Gerasimova, O. A. Lodochnikova, A. R. Burilov, “Efficient synthesis of calix[4]resorcinol <i>rccc</i> diastereoisomers using high amount of trifluoroacetic acid in the chloroform medium”, Mendeleev Commun., 2023, Volume 33, Issue 6,Pages <nobr>844

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Communications

Efficient synthesis of calix[4]resorcinol rccc diastereoisomers using high amount of trifluoroacetic acid in the chloroform medium

I. R. Knyazeva^a, N. P. Romashov^b, V. V. Syakaev^a, D. P. Gerasimova^a, O. A. Lodochnikova^a, A. R. Burilov^a

^a A.E. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of the Russian Academy of Sciences, Kazan, Russian Federation
^b Kazan National Research Technological University, Kazan, Russian Federation

Abstract: The use of excess of trifluoroacetic acid in chloroform (1 : 1, v/v) in a one-pot acid-catalyzed cyclocondensation of functionalized benzaldehydes with 2-methylresorcinol significantly improves the yield of calix[4]resorcinol rccc diastereoisomers compared to rctt ones. The fraction and yield of the rccc isomers sometimes approach 100% along with shortening the reaction time. The structure of new rccc diastereoisomer of chlorine-containing calix[4]resorcinol has been established by single crystal X-ray diffraction.

Keywords: calix[4]resorcinols, condensation, conformation, rccc diastereoisomer, rctt diastereoisomer.

Language: English

DOI: 10.1016/j.mencom.2023.10.035

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