Direct transformation of 5-hydroxymethylfurfural to the building blocks 2,5-dihydroxymethylfurfural (DHMF) and 5-hydroxymethyl furanoic acid (HMFA) via Cannizzaro reaction

An efficient, simple, scalable and atom efficient method for the synthesis of 2,5-dihydroxymethylfuran (DHMF) and 5-hydroxymethylfuranoic acid, as sodium salt (HMFA), in 80% yield from 5-hydroxymethylfurfural (HMF) in water using NaOH (0.9 eq.) via a Cannizzaro reaction is described. Both the buildi...

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Published inGreen chemistry : an international journal and green chemistry resource : GC Vol. 15; no. 10; pp. 2849 - 2853
Main Authors Subbiah, Sowmiah, Simeonov, Svilen P., Esperanca, Jose M. S. S., Rebelo, Luis Paulo N., Afonso, Carlos A. M.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2013
Royal Society of Chemistry
Subjects
Chemistry
Chemistry, Multidisciplinary
Exact sciences and technology
Green & Sustainable Science & Technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
Science & Technology - Other Topics
OXIDATION
CHEMISTRY
FRUCTOSE
BIOMASS
CATALYSTS
Reaction product
Crystallization
Furfural(hydroxymethyl)
Maillard reaction
Aldehyde
Oxygen heterocycle
Sodium Compounds
Cannizzaro reaction
Carboxylic acid
Carboxylate
Isolation
Basic medium
Aqueous solution
Synthon
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Summary:An efficient, simple, scalable and atom efficient method for the synthesis of 2,5-dihydroxymethylfuran (DHMF) and 5-hydroxymethylfuranoic acid, as sodium salt (HMFA), in 80% yield from 5-hydroxymethylfurfural (HMF) in water using NaOH (0.9 eq.) via a Cannizzaro reaction is described. Both the building blocks DHMF and HMFA were successfully isolated merely using selective crystallisation.
Bibliography:FCT
ISSN:1463-9262
1463-9270
DOI:10.1039/c3gc40930a