Alkylation furfuryl alcohol

Compounds which are rather unstable. Typical members of this class are 2-furaidehyde, 2-furfuryl alcohol and 2-alkyl furans, the latter being more resistant than the former. The action of acids or oxygen on these derivatives produces appreciable resinification, but, if properly purified and stored in vacuo, they are indefinitely stable25 16s. ... 

Ethers from alkylation of furfuryl alcohol with dihalides were obtained under solvent PTC + MW conditions with quasi-quantitative yields (Eq. 38) [19]. 

Among the various derivatives of biomass, furanic compounds obtained from furfural are important (200,0001 year-1). A new family of furanic diethers has been obtained by alkylation of 2,5-furandimethanol or furfuryl alcohol under microwave irradiation with PTC solvent-free conditions [83] (Scheme 8.59). 

Reaction times were improved by microwave irradiation, and the same conditions were extrapolated to the synthesis of a series of new furanic diethers by alkylation of furfuryl alcohol by dihalides [83],... 

Reaction of 56 with thiols in dichloromethane gives the analogous alkyl-thiomethyl and cycloalkylthiomethyl derivatives [e.g., treatment with ethanethiol gives A -(2-hydroxyethylthiomethyl)vinblastine (57)] (75). Compound 56 is also a useful intermediate for the preparation of N-1-furanyl derivatives. For example, treatment of 56 with furfuryl alcohol in methylene chloride in the presence of trace acid gives N -[(5-hydroxy-methyOfurfuryl]vinblastine (58). 

Addition of 0.5% sodium alkyl sulphate to furfuryl alcohol 14.4 millisec... 

From the molecular beam MS of the pyrolysis products of the P/N fractions, a number of phenolic compounds were detected guaiacol (2-methoxyphenol) (m/z 124), catechols (m/z 110), isomers of substituted 2-methoxyphenols with alkyl groups such as methyl (m/z 138), vinyl (m/z 150), 3-hydroxy-propen(l)-yl (m/z 180), allyl (m/z 164), hydroxyethyl (m/z 168), and ethyl (152), most likely in the para position. In addition, a few carbohydrate-derived components are also present in this fraction such as furfuryl alcohol and other furfural derivatives. 

A large group of the furans and their derivatives have specialty and industrial uses. QO Chemicals, Inc., formerly the Chemicals Division of the Quaker Oats Company, has been the world s largest producer of furfural and its derivatives for many years. In addition to furfural, their commercial products include furfuryl alcohol, tetrahydrofuryl alcohol, tetrahydrofuran, furoic acid and its alkyl furoates, furfural amines, levulinic acid, methylfuran, acetyl furan, meth-yltetrahydrofuran, and various polyetherpolyols and resins. 

Among the various derivatives of biomass, furan compounds obtained from furfural are important (200 000 t year ). A new family of furan diethers has been obtained by alkylation of 2,5-furandimethanol or furfuryl alcohol under the action of microwave irradiation with PTC solvent-free conditions (Scheme 10.79) [154]. Reaction times were improved by use of microwave irradiation, and the same conditions were extrapolated to the synthesis of a series of new furan diethers by alkylation of furfuryl alcohol by dihalides. 1,4-Diketones substituted by furans or thiophenes were synthesized by conjugate addition of aldehydes to a,j8-unsaturated ketones by irradiation without solvent in the presence of thiazolium halides and DBU adsorbed on alumina [155]. 

Jurczak and co-workers prepared chiral furfuryl alcohols via the Friedel-Crafts reaction. Treatment of 2-methylfliran with alkyl glyoxylates in the presence of a salen-cobalt(II) complex under high pressure provided the desired product in 47% yield with modest enantioselectivity. 

The aldehyde group stabilizes the furfural stmcture against the acid-catalyzed fission of the furan ring that readily occurs in furan and alkyl furan derivatives. Basic-type stabilizers, such as tertiary amines, can be used to inhibit oxidation of the furan structure [3]. Furfural can be oxidized to furoic acid or reduced to furfuryl alcohol which can be converted to furan by a catalyzed decarbonylation reaction. On an industrial scale furfural is the source for furfuryl alcohol, tetrahydrofurfuryl alcohol, furan, and tetrahydrofuran. Nitro-furan compounds derived from furfural are used as bactericides in humans. 

Intrinsic energy of FA can also be upgraded by means of etherification with short-chain alcohols, transformation of alkyl-furfuryl ethers into alkyl levulinates and esterification with short alkyl carboxylic acids. In the following, we wiU discuss the most... 

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