Jump to main content
Jump to site search

Issue 39, 2017, Issue in Progress
Previous Article Next Article

Sulfuric acid and Amberlyst-H+ catalyzed condensation reactions of renewable keto acids with paraformaldehyde: synthesis of a new dispiro bis-lactone ring system 2,9,13-trioxadispiro[4.1.4.3]tetradecane-3,6,10-trione

Author affiliations

Abstract

The sulfuric acid and Amberlyst-H+ catalyzed condensation reactions of renewable feedstock levulinic acid with paraformaldehyde under neat conditions at 80 °C gives 2,9,11,14-tetraoxadispiro[4.1.5.3]pentadecane-3,6-dione in 91–93% yield, in which the structure was confirmed by single crystal X-ray crystallography. A similar condensation reaction between 4-ketopimelic acid and paraformaldehyde at 80 °C gives 2,9,13-trioxadispiro[4.1.4.3]tetradecane-3,6,10-trione. This new dispiro bis-lactone was found to composed of a 1.6 : 1 mixture of isomers with planes of symmetry bisecting the tetrahydro-2H-pyran-4-one rings through the carbonyl groups.

Graphical abstract: Sulfuric acid and Amberlyst-H+ catalyzed condensation reactions of renewable keto acids with paraformaldehyde: synthesis of a new dispiro bis-lactone ring system 2,9,13-trioxadispiro[4.1.4.3]tetradecane-3,6,10-trione

Back to tab navigation

Supplementary files

Publication details

The article was received on 24 Feb 2017, accepted on 19 Apr 2017 and first published on 03 May 2017


Article type: Paper
DOI: 10.1039/C7RA02303K
RSC Adv., 2017,7, 23917-23923
  • Open access: Creative Commons BY-NC license
  •   Request permissions

    Sulfuric acid and Amberlyst-H+ catalyzed condensation reactions of renewable keto acids with paraformaldehyde: synthesis of a new dispiro bis-lactone ring system 2,9,13-trioxadispiro[4.1.4.3]tetradecane-3,6,10-trione

    A. S. Amarasekara, U. Ha, M. S. Fonari, S. N. Bejagam and D. Margetić, RSC Adv., 2017, 7, 23917
    DOI: 10.1039/C7RA02303K

    This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material and it is not used for commercial purposes.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements