Communications

Moving of the tetramethylbutanediyl substituent over the catecholcarbaldehyde core

M. A. Zherebtsov, N. D. Anisimova, A. E. Tarakanova, M. V. Arsenyev, S. A. Chesnokov

G. A. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, 603137 Nizhny Novgorod, Russian Federation

Abstract: 1,1,4,4-Tetramethylbutane-1,4-diyl substituent fused to positions 5,6 of 2,3-dihydroxybezaldehyde (‘catecholcarbaldehyde’) upon the action of acids readily moves to positions 3,4 to afford less strained isomer, with the optimum reagent being neat methanesulfonic acid acting at room temperature. The same compound was prepared in four steps from 3,4-(1,1,4,4-tetramethylbutane-1,4-diyl)phenol; the intermediates were the mixtures of 3,4- and 4,5-fused o-benzoquinones/catechols whereas the last step involved the abovementioned substituent moving.

Keywords: catechols, o-quinones, catecholcarbaldehyde, alkylation, oxidation, reduction.

Received: 05.06.2025
Accepted: 22.07.2025

Language: English

DOI: 10.71267/mencom.7838

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