4208-54-2

Usage

Physical state

Yellow liquid

Odor

Strong, sweet, and caramel-like

Usage

Flavor and fragrance industry as a flavoring agent

Additional uses

Production of resins, plastics, and pharmaceuticals

Production source

Furfuryl alcohol from biomass sources like corn cobs and sugarcane

Health concern

Potential human carcinogen

Safety precaution

Handle and use with caution

Upstream product

• 110-00-9 furan 
• 1538-75-6 2,2-dimethylpropanoic anhydride 
• 630-18-2 tert-butyl isocyanide 
• 4208-53-1 2-methyl-1-(2-furyl)-1-propanone 
• 74-88-4 methyl iodide 
• 3282-30-2 pivaloyl chloride 
• 4229-84-9 α-(1,1-dimethylethyl)furan-2-methanol 
• 98-01-1 furfural 
• 84379-72-6 1,3-dioxoisoindolin-2-yl 3,3-dimethylbutanoate 
• 118486-94-5 2-(tributylstannyl)furan 

Downstream Products

• 76908-05-9 2-(2-furyl)-3,3-dimethyl-1-phenylbutan-2-ol 
• 76908-12-8 1-(3-benzyl-2-furyl)-2,2-dimethylpropan-1-one 
• 556811-68-8 1-(2'-furyl)-2,2-dimethylpropan-1-one tosyl hydrazone 
• 556811-67-7 1-(2'-furyl)-2,2-dimethylpropan-1-one benzenesulfonyl hydrazone 
• 556811-69-9 1-(2'-furyl)-2,2-dimethylpropan-1-one 4-methoxybenzenesulfonyl hydrazone 
• 188772-60-3 (Z)-1-(furan-2-yl)-2,2-dimethylpropan-1-one O-benzyloxime 
• 331852-24-5 (R)-1-(furan-2-yl)-2,2-dimethylpropanamine 
• 63688-34-6 2-tert-butyl-pyridin-3-ol 

Relevant academic research and scientific papers

Chemoenzymatic approach to optically active 4-hydroxy-5-alkylcyclopent-2- en-1-one derivatives: An application of a combined circular dichroism spectroscopy and DFT calculations to assignment of absolute configuration

A series of representative optically active derivatives of 4-hydroxy-5-alkylcyclopent-2-en-1-one were prepared from the respective 2-furyl methyl carbinols via the Piancatelli rearrangement followed by the enzymatic kinetic resolution of racemates. Applicability of chiroptical methods (experimental and calculated electronic circular dichroism [ECD] and vibrational circular dichroism [VCD] spectra) to determine the absolute configuration of both stereogenic centers in 4-hydroxy-5-methylcyclopent-2-en-1-one was demonstrated. It was also demonstrated that the concurrent application of ECD and VCD spectroscopy can be used for the determination of the configuration of two stereogenic centers. Chirality 26:300-306, 2014. 2014 Wiley Periodicals, Inc.

Iron-Catalyzed Oxidative Decarbonylative α-Alkylation of Acyl-Substituted Furans with Aliphatic Aldehydes as the Alkylating Agents

A protocol for FeCl2-catalyzed oxidative decarbonylative α-alkylation of acyl furans using alkyl aldehydes as the alkylating agents has been developed. This protocol affords α-alkyl-α-acylfurans in moderate to good yields in a practical and sustainable fa

N-Heterocyclic Carbene-Catalyzed Decarboxylative Alkylation of Aldehydes

We found that N-heterocyclic carbene catalysis promoted the unprecedented decarboxylative coupling of aryl aldehydes and tertiary or secondary alkyl carboxylic acid-derived redox-active esters to produce aryl alkyl ketones. The mild and transition-metal-free reaction conditions are attractive features of this method. The power of this protocol was demonstrated by the functionalization of pharmaceutical drugs and natural product. A reaction pathway involving single electron transfer from an enolate form of Breslow intermediate to a redox ester followed by recombination of the resultant radical pair to form a carbon-carbon bond is proposed.

Deprotonative metalation of functionalized aromatics using mixed lithium-cadmium, lithium-indium, and lithium-zinc species

In situ mixtures of CdCl2TMEDA (0.5 equiv; TMEDA = N,N,N',N'-tetramethylethylenediamine) or InCl3 (0.33 equiv) with [Li(tmp)] (tmp = 2,2,6,6-tetramethylpiperidino; 1.5 or 1.3 equiv, respectively) were compared with the previously described mixture of ZnCl2-TMEDA (0.5 equiv) and [Li(tmp)] (1.5 equiv) for their ability to deprotonate anisole, benzothiazole, and pyrimidine. [(tmp)3CdLi] proved to be the best base when used in tetrahydrofuran at room temperature, as demonstrated by subsequent trapping with iodine. The Cd-Li base then proved suitable for the metalation of a large range of aromatics including benzenes bearing reactive functional groups (CONEt2, CO2Me, CN, COPh) or heavy halogens (Br, I), and heterocycles (from the furan, thiophene, pyrrole, oxazole, thiazole, pyridine, and diazine series). Fivemembered heterocycles benefiting from doubly activated positions were similarly dideprotonated at room temperature. The aromatic lithium cadmates thus obtained were involved in palladium-catalyzed cross-coupling reactions or simply quenched with acid chlorides.

RUTHENIUM COMPLEX AND PROCESS FOR PRODUCING TERT-ALKYL ALCOHOL THEREWITH

A tert-alkyl ketone, pinacolone was hydrogenated under pressurized hydrogen in the presence of a ruthenium complex (S)-1 and a base, and corresponding (S)-3,3,-dimethyl-2-butanol was thereby obtained in 100% yield and 97% ee.

Asymmetric hydrogenation of tert-alkyl ketones

A combined system of RuCl2(tolbinap)(pica) and an alkaline or organic phosphazene base catalyzes asymmetric hydrogenation of sterically congested tert-alkyl ketones (TolBINAP = 2,2-bis(di-4-tolylphosphino)-1,1-binaphthyl, PICA = α-picolylamine). Hydrogenation with RuH(η1-BH4)(tolbinap)(pica) does not require any strong base. Alcoholic solvents strongly affect the catalytic efficiency. The reaction proceeds smoothly in ethanol under 1-20 atm of H2 and at room temperature with a substrate to catalyst molar ratio of up to 100000. Various aliphatic, aromatic, heteroaromatic, and olefinic tert-alkyl ketones are convertible to the corresponding chiral carbinols in high enantiomeric purity. Olefinic and heteroaromatic functions are left intact. Certain cyclic ketones are also usable. The mode of enantioface selection is consistent and predictable. Copyright

Palladium-catalyzed chemoselective cross-coupling of acyl chlorides and organostannanes

Chemoselective cross-coupling of aliphatic and aromatic acyl chlorides with aryl-, heteroaryl-, and alkynylstannanes proceeds in up to 98% yield using 2.5 mol % of bis(di-tert-butylchlorophosphine)palladium(II) dichloride as the precatalyst. Various functional groups including aryl chlorides and bromides that usually undergo oxidative addition to palladium complexes bearing phosphinous acid or dialkylchlorophosphine ligands are tolerated. This procedure allows convenient ketone formation and eliminates inherent limitations of Friedel-Crafts acylations such as substituent-directing effects and typical reactivity requirements of Lewis acid-catalyzed electrophilic aromatic substitutions.

Facile synthesis of pivalophenones by an ultrasound assisted iodine catalysed Friedel-Crafts acylation reaction

The use of ultrasound in the acylation reactions of various aromatics and heterocyclics with pivaloyl chloride in the presence of catalytic amount of iodine, without any added solvent and at room temperature, gives excellent yields of the respective pivalophenones in a short reaction time.

A facile synthesis of pivalophenones by ultrasound assisted AlCl3 catalysed Friedel-Crafts reaction

Pivalophenones have been prepared by the acylation reaction of various aromatic and heterocyclic compounds with pivaloyl chloride using AlCl3 as catalyst under sonochemical conditions in a short reaction time and in reasonable yields.

ALKYLATION OF 2-ACETYLFURAN AND 2-ACETYLTHIOPHENE UNDER THE CONDITIONS OF PHASE-TRANSFER CATALYSIS

The reactions of 2-acetylfuran and 2-acetylthiophene with alkyl and benzyl halides in two-phase liquid-solid system (benzene or toluene-solid potassium hydroxide) in the presence of 18-crown-6-polyether at room temperature give the corresponding ketones (