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 › peer-review

94 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

Access to Document

10.1039/c3gc40930a

Cite this

@article{4ddc7b15bb294fd4bc5b90865d26a2d5,

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

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.",

keywords = "BIOMASS, FRUCTOSE, CHEMISTRY, CATALYSTS, OXIDATION",

author = "Esperanca, {Jose Manuel} and Rebelo, {Luis Paulo}",

year = "2013",

month = jan,

day = "1",

doi = "10.1039/c3gc40930a",

language = "Unknown",

volume = "15",

pages = "2849--2853",

journal = "Green Chemistry",

issn = "1463-9262",

publisher = "ROYAL SOC CHEMISTRY",

number = "10",

}

TY - JOUR

T1 - Direct transformation of 5-hydroxymethylfurfural to the building blocks 2,5-dihydroxymethylfurfural (DHMF) and 5-hydroxymethyl furanoic acid (HMFA) via Cannizzaro reaction

AU - Esperanca, Jose Manuel

AU - Rebelo, Luis Paulo

PY - 2013/1/1

Y1 - 2013/1/1

N2 - 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.

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

U2 - 10.1039/c3gc40930a

DO - 10.1039/c3gc40930a

M3 - Article

VL - 15

SP - 2849

EP - 2853

JO - Green Chemistry

JF - Green Chemistry

SN - 1463-9262

IS - 10

ER -