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

Jose Manuel Esperanca; Luis Paulo Rebelo

doi:10.1039/c3gc40930a

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

Jose Manuel Esperanca, Luis Paulo Rebelo

Instituto de Tecnologia Química e Biológica António Xavier (ITQB)

Research output: Contribution to journal › Article

87 Citations (Scopus)

Abstract

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.

Original language	Unknown
Pages (from-to)	2849-2853
Journal	Green Chemistry
Volume	15
Issue number	10
DOIs	https://doi.org/10.1039/c3gc40930a
Publication status	Published - 1 Jan 2013

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10.1039/c3gc40930a

Cite this

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abstract = "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.",

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AU - Rebelo, Luis Paulo

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AB - 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.

KW - BIOMASS

KW - FRUCTOSE

KW - CHEMISTRY

KW - CATALYSTS

KW - OXIDATION

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