Mechanistic study of the aldol condensation occurring in the alkaline solution of 3-hydroxy 2-oxo propranoate (β hydroxypyruvate)

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Abstract

With 3-bromo-2-oxopropanoate (β bromopyruvate) and its ethyl ester, the ionisation of the gemdiol of the hydrated form BrCH2-C(OH)2-COOR 1 initiates the elimination of bromide anion yielding 3-hydroxy-2-oxopropanoate 2 (β-hydroxypyruvate). The mechanism of the reaction was investigated essentially by polarography in aqueous solution. In neutral (and acid) media, the polarographic behaviour of 2 resembled that of other α-ketoacids: reduction at the mercury electrode yielded glycerate. In alkaline media, there was evidence of the carbanion enolate -O-CHC(OH)-COO-. 3'. The overall rate constant was determined according to a kinetic law of the typer:v = k.|2|.|OH-|; found k = 1,56 min-1 in NaOH 0.5 N at 25°. In the pH range 10.5 to 11.5,3' existed in minor amounts and initiated a slow aldol condensation with the tautomer 3-oxo-2-hydroxypropanoate 4 (tartronate Semialdehyde) according to a kinetic law of the type v = k̄.|2|2.|OH-|found k̄ = 211.mol-1 min -1 at 25°, at pH 11.0. The aldol product was isolated as a sodium sail and its structure established by 13C NMR. © 1981.

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Fleury, D., Fleury, M. B., & Platzer, N. (1981). Mechanistic study of the aldol condensation occurring in the alkaline solution of 3-hydroxy 2-oxo propranoate (β hydroxypyruvate). Tetrahedron, 37(3), 493–501. https://doi.org/10.1016/S0040-4020(01)92421-4

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