Catalytic synthesis of bioactive 2H chromene alcohols from (−) isopulegol and acetone on sulfonated clays

Mathias Laluc, Päivi Mäki-Arvela, Andrea F. Peixoto, Nikolai Li Zhulanov, Thomas Sandberg, Nariman F. Salakhutdinov, Konstantin Volcho, Cristina Freire, Alexander Yu. Sidorenko, Dmitry Murzin

Research output: Contribution to journalArticleScientificpeer-review

1 Citation (Scopus)

Abstract

Condensation of (−)-isopulegol with acetone was investigated at 25–40 °C over clay based materials (K10, cloisite Na+ and halloysite nanotubes) modified with sulfonic acid groups by one-pot sulfonation with chlorosulfonic acid or via organosilylation with 2-(4-chlrosulfonylphenyl)-ethyltrimethoxysilane. The target product was the R diastereomer of dimethyl-substituted octahydro-2H-chromen-4-ol with exhibits antiviral activity. The catalysts were characterized by a range of physico-chemical methods. The effect of the initial isopulegol concentrations on the yield of ketone-derived chromenols and the R/S isomers ratio was studied for the first time. The best catalyst was a highly acidic, large pore K10-clay modified by sulfonic acid. Varying the initial concentration of the reagents allows to find a balance between dehydration by-products and a side etherification reaction. A high yield (73%) of the desired chromenols was reached using 0.52 mol/l initial (−)-isopulegol concentration after 240 min at 87% substrate conversion and reaction temperature 25 °C. The yield exceeded that of other previously reported in the open literature catalysts.
Original languageEnglish
Pages (from-to)627–644
JournalReaction Kinetics, Mechanisms and Catalysis
Volume129
DOIs
Publication statusPublished - 20 Feb 2020
MoE publication typeA1 Journal article-refereed

Keywords

  • Chemical Engineering

Fingerprint Dive into the research topics of 'Catalytic synthesis of bioactive 2H chromene alcohols from (−) isopulegol and acetone on sulfonated clays'. Together they form a unique fingerprint.

Cite this