Furyl alcohol

In a 500-cc. three-necked flask, fitted with a mechanical stirrer, thermometer, separatory funnel, and calcium chloride tube, are placed 96 g. (56.5 cc., 0.36 mole) of redistilled phosphorus tribromide (b.p. 174-175°/740 mm.) and 50 cc. of dry benzene. From the separatory funnel, 15 g. of dry pyridine is added with stirring over a period of fifteen minutes. The flask is then surrounded by an ice-salt mixture, and the contents are cooled to — 5°. A mixture of 102 g. (1 mole) of redistilled tetrahydrofur-furyl alcohol (b.p. 79-80°/20 mm.) and 5 g. of dry pyridine (total pyridine, 20 g., 0.25 mole) is added slowly from the dropping funnel with stirring over a period of four hours. During this time the internal temperature is kept at —5° to —3°. Stirring is continued for one hour longer, and the cooling bath is then allowed to warm up to room temperature. 

Many of the reactions of A-chloro- and A-bromo-imides are extremely violent or explosive. Those observed include A-chlorosuccinimide with aliphatic alcohols or benzylamine or hydrazine hydrate A-bromosuccimmidc with aniline, diallyl sulfide, or hydrazine hydrate or 3-nitro-A-bromophthalimide with tetrahydrofur-furyl alcohol l,3-dichloro-5,5-dimethyl-2,4-imidazolidindione with xylene (violent explosion). Individually indexed compounds are ... 

Synonyms AI3-01171 BRN 0106291 CCRIS 2922 EINECS 202 626-1 FEMA No. 2491 2-Furan carbinol 2-Furanmethanol Furfural alcohol Furyl alcohol Furyl carbinol 2-Furyl carbi-nol a-Furyl carbinol 2-Furylmethanol 2-Hydroxymethylfuran NCI-C56224 NSC 8843 UN 2874. 

This conversion of readily available 2-furyl alcohols into unsaturated pyranosuloses proved a very effective route to racemic monosaccharides, through stepwise, selective functionalization of the enone grouping in 325. The shortest synthesis of a natural compound by following this scheme involves palladium-catalyzed hydrogenation of the aldosulose (325, R = Me) obtained from l-(2-furyl)ethanol, resulting209 in cinerulose A, the sugar component of the antibiotic cine-rubin. 

Saponification of the product with standard potassium hydroxide shows 93-94 per cent ester. It contains some fur-furyl alcohol, the removal of which by fractional distillation is difficult, because the boiling points of the alcohol (i6g°/752 mm.) and the ester (175°/764 mm.) are so close together. Furfuryl acetate darkens on standing. It may be redistilled with little loss to give an almost colorless product. 

Alcohols are practically inert towards DIB at room temperature and react very slowly at elevated temperature, unless they possess special features. Thus, oxidation due to the presence of furan ring occurred in a series of furyl alcohols which with DIB alone or better in combination with magnesium perchlorate (in a molar ratio 1 2) were converted into pyran-3(6//)-ones [129]. 

Many industrial applications utilize the solvent properties of furfural and fur-furyl alcohol however, both chemicals also display unique features as monomers for condensation polymerization. Most of the furfuryl alcohol sold is used as monomer in the manufacture of resins for industrial application. 

SYNS 2-FURANCARBINOL 2-FURANMETHANOL FURFURAL ALCOHOL 2-FURFURYLALKOHOL (CZECH) FURYL ALCOHOL a-FURAXCARBINOL 2-FUR iXCARBINOL (2-FL RYL)METHANOL 2-HYDROXYMETHYLFURAN NCI-C56224... 

Enantioselective addition of dialkylzinc to furyl aldehydes using DBNE as a chiral catalyst affords optically active furyl alcohols in up to 94% ee (eqs 15 and 16). ... 

Since the enolization is not restricted to the 2 and 3 positions, a number of products are formed that undergo subsequent aldol condensations and the Cannizzaro oxidation. They are all 2-hydroxy-3-methyl, 3,4-dimethyl-2-hydroxy, 3,5-dimethyl-2-hydroxy, and 3-ethyl-2-hydroxy-2-cyclopenten-l-ones sugar acids acetic acid hydroxyacetone three isomeric hydroxy-2-butanones y-butyrolactone and such furan derivatives as furyl alcohol, 5-methyl-2-furyl alcohol, and 2,5-dimethyl-4-hydroxy-3(2H)-furanone. They are food flavoring agents. 

The oxidation of 2-furyl alcohols 33 using (-t-)-DIPT as a chiral source provides (l )-furyl alcohols of >95% ee and pyranone when 0.6 equivalents of TBHP are used [73,74]. This stereochemistry is consistent with the empirical rules for kinetic resolution of secondary allyUc alcohols (Scheme 11). Both the optically... 

Kinetic resolution of 2-thienyl alcohols 46 is also performed efficiently [78]. Differing from kinetic resolution of racemic 2-furyl alcohols, however, a stoichi-... 

The asymmetry in 5-hydroxy-5,6-dihydropyran-2-ones, which form the basis of the phomopsolides, is derived from the Noyori asymmetric hydrogenation of a furyl ketone. The resulting furyl alcohol is then stereoselectively transformed into the pyranone <04TL1005>. 

When furfuryl alcohol was added as a comonomer to the THEIC, water fluxes were increased tenfold. In addition, the extremely high salt rejections characteristic of NS-200 were obtained, while the high organic rejections characteristic of the isocyanurate moiety were retained. A typical patent example of membrane fabrication uses a water solution of 1 2 2 1 weight percent THEIC fur-furyl alcohol sulfuric acid dodecyl sodium sulfate, deposited on microporous polysulfone and cured at 150°C for 15 minutes. This membrane, possessing a thin active layer 100 to 300 angstroms thick, showed 99.9% rejection and 12 gfd flux under seawater test conditions at 1,000 psi. 

Tetrahy drofurf uryI Alcohol- Tetrahydro-2-furan-melhanol tetrahydro-2-furancarbinol tetrahydro-2-furyl-methanol THFA. C,HI0Oj mol wt 102.13. C 58.80%, H 9.87%, O 31.33%. Prepn by catalytic hydrogenation of fur-furyl alcohol Lukes. Nelson, J. Org. Chem. 21, 1096 (1956). Manuf by catalytic hydrogenation of furfural or furfuryl alcohol Dunlop. Schegulla, U.S. pat. 2,838,523 (1958 to Quaker Oats). Occurs in two isomeric forms D-isomer... 

In general it is aldehydes of aromatic hydrocarbons and of heterocycles that can be subjected to this reaction, named after its discoverer the Cannizzaro reaction but there a similar oxidation-reduction, brought about by an enzyme, plays an important part in biological events in the cell. In the laboratory the Cannizzaro reaction serves for preparation of both acids and alcohols, each normally in 50% yield. As example, the preparation of 2-furoic acid and fur-furyl alcohol from 2-furaldehyde is here recorded.499... 

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