4.4 Article

Acid catalyzed condensation of levulinic acid with glyoxylic acid: synthesis of 1-methyl-2,8-dioxabicyclo[3.3.0]oct-4-ene-3,7-dione

Journal

TETRAHEDRON LETTERS
Volume 57, Issue 24, Pages 2598-2600

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2016.04.103

Keywords

Levulinic acid; Glyoxylic acid; Aldol condensation; Polyester monomer; Bis-lactone

Funding

  1. National Science Foundation grants [CBET-0929970, CBET-1336469, HRD-1036593]
  2. United States Department of Agriculture grant [CBG-2010-38821-21569]
  3. Direct For Education and Human Resources
  4. Division Of Human Resource Development [1036593] Funding Source: National Science Foundation
  5. Div Of Chem, Bioeng, Env, & Transp Sys
  6. Directorate For Engineering [1336469] Funding Source: National Science Foundation

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The sulfuric acid catalyzed condensation of levulinic acid with glyoxylic acid at 80 degrees C, for 24 h under neat conditions gives 1-methyl-2,8-dioxabicyclo[3.3.0]oct-4-ene-3,7-dione in 92% yield. Catalytic reduction of this unsaturated bis-lactone provides a facile route to produce polyester monomer 1-methyl-2,8-dioxabicyclo[3.3.0]octane-3,7-dione from renewable feedstocks. (C) 2016 Elsevier Ltd. All rights reserved.

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