1,1-Bis[2-furyl]ethanes from 1-(2-Furyl)-ethanols

Balaban, Alexandrù T.; Bota, Anisia; Zlota, Andrei

doi:10.1055/s-1980-28948

Cited by 9 publications

(4 citation statements)

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“…68,69 Other Lewis acids that are air stable and water tolerant have also been reported for the Diels-Alder reaction of furan with suitable dienophiles. [70][71][72] The above highlight can be said to have established the platform for the application of Diels-Alder reactions for the formation of C 12 -biofuel intermediates exclusively from HMF. A C 12 or C 10 biofuel intermediate can be formed via the hetero Diels-Alder condensation of two HMF or furfural molecules respectively with a furan ring as the diene and the carbonyl group as the dienophile.…”

Section: Cross-condensation Of Hmf (Non C-c Coupling)mentioning

confidence: 99%

Towards the conversion of carbohydrate biomass feedstocks to biofuels via hydroxylmethylfurfural

James

Maity

Usman

et al. 2010

Energy Environ. Sci.

184

109

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This review appraises the chemical conversion processes recently reported for the production of hydroxylmethylfurfural (HMF), a key biorefining intermediate, from carbohydrate biomass feedstocks. Catalytic sites or groups required for the efficient and selective conversion of hexose substrates to HMF are examined. The principle of concerted catalysis was used to rationalise the dehydration of fructose and glucose to HMF in non-aqueous media. A survey of reported reaction routes to diesel-range biofuel intermediates from HMF or furfural is presented and self-condensation reaction routes for linking two or more HMF and furfural units together toward obtaining kerosene and diesel-range biofuel intermediates are highlighted. The reaction routes include: benzoin condensation, condensation of furfuryl alcohols, hetero Diels-Alder reaction and ketonisation reaction. These reaction routes are yet to be exploited despite their potential for obtaining kerosene and diesel-range biofuel intermediates exclusively from furfural or hydroxylmethylfurfural.

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Section: Cross-condensation Of Hmf (Non C-c Coupling)mentioning

confidence: 99%

Towards the conversion of carbohydrate biomass feedstocks to biofuels via hydroxylmethylfurfural

James

Maity

Usman

et al. 2010

Energy Environ. Sci.

184

109

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“…On the other hand, there are also reports of excellent yields for the preparation of bis(2-furyl)alkanes from 3-, 5-alkyl-, and 3,5-dialkyl-substituted 2-furylalkanols (Scheme 1). These reactions proceed in the presence of polyphosphoric acid, 14 silver(I) ions or trichloroacetic acid. 15 Some bis(5-aryl-2-furyl)methanes have been reported to show tuberculostatic activity, but these compounds were obtained only as by-products of some reactions.…”

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confidence: 99%

(Aryl)(2-furyl)alkanes and their derivatives, 20. Synthesis of symmetric bis- and tris(2-furyl)methanes

Строганова¹,

Бутин²,

Sorotskaya³

et al. 2000

Arkivoc

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New methods for the synthesis of symmetric 5,5'-disubstituted bis-and 5,5',5"-trisubstituted tris(2-furyl)methanes have been developed. Symmetric bis(2-furyl)methanes were prepared from 5-substituted 2-furylmethanols in the presence of concentrated perchloric acid. The attempted synthesis of (aryl)[bis(2-furyl)]methanes from (aryl)(2-furyl)methanols in the presence of acid catalysts failed. The reaction of 5-substituted 2-furaldehydes with ethylene glycol in the presence of strong acid catalysts led to tris(2-furyl)methanes. Plausible mechanisms of these transformations are discussed.

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“…Difurylmethane derivatives were observed as side products frma the liquid-phase catalytic hydration [84] and decarbonylation of furfurol in the presence of 5% Pd/C [85] and from the electrochemical reduction of 5-methylfurfurol [86]. However, preparative syntheses of 3,5-dialkyl-substituted 2-furylcarbinols in 60-80% yield in the presence of polyphosphoric acid [88], Ag + ions or C13CCOOH [89] were proposed. Hydrothermolysis of alkylfurylcarbinols at 300~ and pH 7 [87] produces the corresponding difurylalkanes in ~15% yield.…”

Section: R= H Mementioning

confidence: 99%

“…The self-condensation of 5-hydroxymethylfurfuryl amine in 5. l M HCI produces the difurylmethane diamine (<10% yield) [50]. Thus, a mechanism including the formation of a carbcation owing to the dehydration of a protonated alcohol with subsequent electrophilic substitution in the 2-position of the furan ring was proposed [86,88,89]. The preparation of the difurylalkane derivatives in all these studies is a side reaction that is of little preparative significance owing to the low yields.…”

Section: R= H Mementioning

confidence: 99%

Furyl(aryl)methanes and their analogs. (Review)

Бутин¹,

Строганова²,

Kul'nevich³

1999

Chem Heterocycl Compd

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FURYL(ARYL)METHANES AND THEIR ANALOGS. (REVIEW) A. V. Butin, T. A. Stroganova, and V. G. Kul'nevich The literature data on furyl(arv. Omethanes are svstematized and analyzed for the first time. Results obtained by the authors on the synthesis, reactions, and application of these compounds are reviewed.~ "XHgCI + ~CH,CI ~ O~~OO I A convenient method for synthesis of difurylmethane is the reaction of furyllithium with furfurol and subsequent reduction of the intermediate carbinol with . It was noted that this is the optimal method for synthesis of difurylmethane because the product yield is 64% and the undesirable side products are

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1,1-Bis[2-furyl]ethanes from 1-(2-Furyl)-ethanols

Cited by 9 publications

References 0 publications

Towards the conversion of carbohydrate biomass feedstocks to biofuels via hydroxylmethylfurfural

Towards the conversion of carbohydrate biomass feedstocks to biofuels via hydroxylmethylfurfural

(Aryl)(2-furyl)alkanes and their derivatives, 20. Synthesis of symmetric bis- and tris(2-furyl)methanes

Furyl(aryl)methanes and their analogs. (Review)

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