Cyclopentanone Derivatives from 5-Hydroxymethylfurfural via 1-Hydroxyhexane-2,5-dione as Intermediate

Bartosz Wozniak; Anke Spannenberg; Yuehui Li; Sandra Hinze; Johannes G de Vries

doi:10.1002/cssc.201702100

Cyclopentanone Derivatives from 5-Hydroxymethylfurfural via 1-Hydroxyhexane-2,5-dione as Intermediate

ChemSusChem. 2018 Jan 23;11(2):356-359. doi: 10.1002/cssc.201702100. Epub 2017 Dec 29.

Authors

Bartosz Wozniak¹, Anke Spannenberg¹, Yuehui Li², Sandra Hinze¹, Johannes G de Vries¹

Affiliations

¹ Leibniz-Institut für Katalyse e.V. an der, Universität Rostock, Albert-Einstein-Str. 29a, 18059, Rostock, Germany.
² State Key Laboratory for Oxo Synthesis and Selective Oxidation, Institute of LICP, Lanzou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou, 730000, P. R. China.

PMID: 29235723
DOI: 10.1002/cssc.201702100

Abstract

An efficient strategy for the conversion of biomass derived 5-hydroxymethylfurfural (HMF) into 2-hydroxy-3-methylcyclopent-2-enone (MCP) by an intramolecular aldol condensation of 1-hydroxyhexane-2,5-dione (HHD) has been developed. Further transformations of MCP towards the diol, enol acetate, levulinic acid and N-heterocyclic compounds are also reported.

Keywords: biomass; cycloketones; homogeneous catalysis; platform chemicals; renewable resources.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Biomass
Catalysis
Cyclopentanes / chemistry*
Furaldehyde / analogs & derivatives*
Furaldehyde / chemistry
Hexanes / chemistry*
Hydrogen Bonding
Models, Molecular
X-Ray Diffraction

Substances

Cyclopentanes
Hexanes
cyclopentanone
5-hydroxymethylfurfural
Furaldehyde