Development of Homogeneous Carboxylation of Phenolates via Kolbe–Schmitt Reaction DOI Creative Commons

Dmitry A. Merzliakov,

Michael S. Alexeev,

Maxim A. Topchiy

et al.

Molecules, Journal Year: 2025, Volume and Issue: 30(2), P. 248 - 248

Published: Jan. 10, 2025

In this study, the homogeneous carboxylation of potassium, sodium, and lithium phenolates in DMSO solution at 100 °C by Kolbe-Schmitt reaction was investigated. The impact water, phenolate concentration, cation nature on yield products selectivity demonstrated. Based patterns observed, it concluded that a complex cluster mechanism governs solution. use medium allowed for convenient testing various additives to assess their reaction. Basic such as sodium salts mesitol, tert-butylcalix[4]arene, isopropyl, tert-butyl cabonates were found enhance reaction, increasing hydroxybenzoic acids 20% (to 61.6%). main product identified 4-hydroxybenzoic acid, contrast classical method which typically yields 2-hydroxybenzoic (salicylic) acid. 13C NMR spectroscopy enabled observation "carbonate complex" first time, with carbonate carbon displaying chemical shift value 142 ppm, an unusual finding stable carbonates, located between signals free dissolved CO2 carboxylate derivatives.

Language: Английский

Development of Homogeneous Carboxylation of Phenolates via Kolbe–Schmitt Reaction DOI Creative Commons

Dmitry A. Merzliakov,

Michael S. Alexeev,

Maxim A. Topchiy

et al.

Molecules, Journal Year: 2025, Volume and Issue: 30(2), P. 248 - 248

Published: Jan. 10, 2025

In this study, the homogeneous carboxylation of potassium, sodium, and lithium phenolates in DMSO solution at 100 °C by Kolbe-Schmitt reaction was investigated. The impact water, phenolate concentration, cation nature on yield products selectivity demonstrated. Based patterns observed, it concluded that a complex cluster mechanism governs solution. use medium allowed for convenient testing various additives to assess their reaction. Basic such as sodium salts mesitol, tert-butylcalix[4]arene, isopropyl, tert-butyl cabonates were found enhance reaction, increasing hydroxybenzoic acids 20% (to 61.6%). main product identified 4-hydroxybenzoic acid, contrast classical method which typically yields 2-hydroxybenzoic (salicylic) acid. 13C NMR spectroscopy enabled observation "carbonate complex" first time, with carbonate carbon displaying chemical shift value 142 ppm, an unusual finding stable carbonates, located between signals free dissolved CO2 carboxylate derivatives.

Language: Английский

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