Abstract
Products of the reactions of 4- and 2-hydroxy-3,5-di-tert-butyl-benzaldehydes with malonic acid, diethyl malonate, and acetic anhydride in the presence of weak bases were isolated and identified. The reactions of 3,5-di-tert-butyl-4-hydroxybenzaldehyde with malonic acid and acetic anhydride in the presence of sodium acetate and piperidine gave 3,5-di-tert-butyl-4-hydroxycinnamic acid. The reaction of its 2-hydroxy isomer with acetic anhydride stopped at the stage of formation of the corresponding O-acetyl derivative, while in the reaction with malonic acid the corresponding substituted cinnamic acid and its lactone (coumarin derivative) were formed as intermediate products in a transformation sequence finally leading to 3-(3,5-di-tertbutyl-2-hydroxyphenyl)-3-piperidinopropionic acid and 6,8-di-tert-butyl-2-oxo-3,4-dihydro-2H-chromen-4-ylacetic acid. Analogous differences were typical of reactions of isomeric 4- and 2-hydroxy-3,5-di-tert-butylbenzaldehydes with diethyl malonate. The transformations of the 2-hydroxy isomer were accompanied by hydrolysis and formation of an adduct of intermediate coumarin derivative with diethyl malonate and piperidine.
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Vol’eva, V.B., Belostotskaya, I.S., Komisarova, N.L., Kurkovskaya, L.N., Pleshkova, A.P., and Prokof’eva, T.I., Russ. J. Org. Chem., 2007, vol. 43, p. 1488.
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Original Russian Text © V.B. Vol’eva, I.S. Belostotskaya, N.L. Komissarova, L.N. Kurkovskaya, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 6, pp. 814–817.
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Vol’eva, V.B., Belostotskaya, I.S., Komissarova, N.L. et al. Anionic condensations of 3,5-di-tert-butyl-4(2)-hydroxybenzaldehydes in the presence of weak bases. Russ J Org Chem 44, 803–806 (2008). https://doi.org/10.1134/S1070428008060043
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DOI: https://doi.org/10.1134/S1070428008060043