Heterogeneous catalysis for transformation of biomass derived compounds beyond fuels: synthesis of monoterpenoid dioxinols with analgesic activity

Alexandra Torozova, Päivi Mäki-Arvela, Atte Aho, Narendra Kumar, Annika Smeds, Markus Peurla, Rainer Sjöholm, Ivo Heinmaa, Dina V. Korchagina, Konstantin P. Volcho, Nariman F. Salakhutdinov, Dmitry Murzin

Research output: Contribution to journalArticleScientificpeer-review

15 Citations (Scopus)

Abstract

Catalytic synthesis of a dioxinol compound, (2S,4aR,8R,8aR)-4,4,7-trimethyl-2-phenyl-4a,5,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-8-ol, exhibiting analgesic activity was demonstrated over Femodified beta zeolite. During interactions between cis-verbenol oxide and benzaldehyde, two main reactions occurred. In the first reaction, namely isomerization of verbenol oxide both cyclopentenic hydroxyketone, oxetane as well as a cyclohexyl compound, (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol were formed. In the second parallel reaction the target compound was generated. The highest yield of the target compound was achieved in the reaction between verbenol oxide and benzaldehyde at their molar ratio of 1:133 with the bifunctional iron modified Fe-H-Beta-150 catalyst at 70 degrees C giving a much higher yield than reported earlier in the literature, being 46 mol-% at complete conversion of verbenol oxide.
Original languageUndefined/Unknown
Pages (from-to)48–55
Number of pages8
JournalJournal of Molecular Catalysis A: Chemical
Volume397
DOIs
Publication statusPublished - 2015
MoE publication typeA1 Journal article-refereed

Keywords

  • Addition
  • Dioxinol
  • Terpenoid
  • Zeolite

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