Recent Catalytic Advances in the Chemistry of Substituted Furans from Carbohydrates and in the Ensuing Polymers

Abstract

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Synthesis of 5-Acetoxymethyl- and 5-Hydroxymethyl-2-vinyl-furan

“…5-Hydroxymethyl-2-vinylfuran (5) was obtained after hydrolysis. The products were characterized by NMR, FTIR and mass spectroscopy data, which agreed with those reported in the literature [1,2]. The MS peaks at 355.219 (5) and 439.224 (7) indicate that both furfuryl derivates spontaneously undergo trimerisation with elemination of a hydroxy (5) and acetate group (7), respectively, under the experimental conditions of the ESI mass spectral analysis.…”

“…The residue was washed several times with water and extracted with chloroform. The extract was dry Na 2 …”

“…Compound 5 has also been prepared by low temperature hydroxyethylation of furfuryl alcohol with a large excess of acetaldehyde, using water as the solvent and a highly dealuminated H-mordenite as catalyst [2]. The mass spectrum of the acetate derivative of 5, 5-acetoxymethyl-2-vinylfuran (7), has been reported [1], but not its preparation, which should be achievable by simple acetylation of the alcohol group.…”

“…5-Hydroxymethyl-2-vinylfuran (5) was first synthesized in 70% overall yield by Dzhemilev et al [1] by the reaction of 2-vinylfuran with 40% aqueous formaldehyde over a catalyst prepared by reducing Pd(acac) 2 (acac = acetylacetonate) with triethylaluminum in the presence of PPh 3 . Compound 5 has also been prepared by low temperature hydroxyethylation of furfuryl alcohol with a large excess of acetaldehyde, using water as the solvent and a highly dealuminated H-mordenite as catalyst [2].…”

5‐hydroxymethylfurfural conversion by fungal aryl‐alcohol oxidase and unspecific peroxygenase

“…The DFF spectrum in DMSO-d 6 ( Fig. S2B) shows only two signals due to the symmetry of the molecule.…”