17678-19-2

Usage

Uses

Used in Chemical Synthesis:
2-Furylhydroxymethylketone is used as a reagent for the preparation of 3-iodocoumarins, which are important compounds in the field of chemical research and development. Its ability to participate in chemical reactions makes it a valuable component in the synthesis process.
Used in Dye Industry:
2-Furylhydroxymethylketone is also used in the preparation of quinoxalines, which are generally utilized in the dye industry. These compounds are known for their ability to impart color to various materials, making them essential in the production of a wide range of dyes.
Used in Pharmaceutical Industry:
In addition to its applications in the dye industry, 2-Furylhydroxymethylketone is also used in the pharmaceutical sector. Its role in the synthesis of quinoxalines, which have potential applications in drug development, highlights its importance in this field. The compound's versatility and reactivity make it a valuable asset in the creation of new pharmaceutical products.

InChI:InChI=1/C6H6O3/c7-4-5(8)6-2-1-3-9-6/h1-3,7H,4H2

Upstream product

• 67-47-0 5-hydroxymethyl-2-furfuraldehyde 
• 144-62-7 oxalic acid 
• 15109-94-1 1-(2-furyl)-2-bromoethanone 
• 21443-46-9 2-diazoacetylfuran 
• 98-01-1 furfural 
• 50-00-0 formaldehyd 
• 1192-62-7 1-(2-furyl)-1-ethanone 
• 62889-08-1 1-(2-furyl)-1-(trimethylsilyloxy)ethylene 
• 7732-18-5 water 
• 57-50-1 Sucrose 
• 552-86-3 furoin 
• 99648-52-9 (2S)-2',2'-dimethyl-2H-pyran-2-spiro-4'-(1',3'-dioxolan)-3(6H)-one 
• 68733-00-6 2,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-1-en-3-ulose 
• 50-99-7 D-glucose 

Downstream Products

• 131496-20-3 (benzoyloxy)methyl 2-furyl ketone 
• 14086-08-9 (R)-2-(2-furyl)-1,2-ethanediol 
• 21036-63-5 4-(2-furyl)-2-phenylthiazole 

Relevant academic research and scientific papers

Direct conversion of cellulose to 1-(furan-2-yl)-2-hydroxyethanone in zinc chloride solution under microwave irradiation

Conversion of cellulose to 1-(furan-2-yl)-2-hydroxyethanone has been demonstrated in concentrated zinc chloride solution under microwave irradiation. Compared with the conventional oil-bath heating mode, microwave irradiation significantly reduced the reaction time and increased the yield of 1-(furan-2-yl)-2-hydroxyethanone. A typical degradation reaction with cellulose produced 1-(furan-2-yl)-2-hydroxyethanone in 12.0% molar yield in ZnCl 2 solution (ZnCl2-H2O ratio = 2.25:1, w/w) with microwave irradiation at 600 W for 5 minutes at 135 °C.

Asymmetric syn-aldol reaction of α-hydroxy ketones with tertiary amine catalysts

The tertiary amine-catalyzed direct asymmetric aldol reaction of 2-hydroxyacetophenones (2-hydroxy-1-arylethanones) with a variety of aliphatic aldehydes has been demonstrated. By using 20 mol-% of unmodified cinchonine as catalyst, the direct aldol reaction products were isolated in good yields and with remarkably high syn diastereocontrol and good asymmetric induction (40-78 % ee). This newly elaborated tertiary-amine-catalyzed direct asymmetric aldol reaction has extended the scope of organocatalytic processes to aromatic α-hydroxy ketones, which have hitherto been unreactive towards enamine catalysis. Unmodified cinchona alkaloids have been found to promote efficiently the direct aldol reaction of hydroxy ketones and various aldehydes in good yields and with remarkably high syn diastereocontrol and good asymmetric induction (40-78 % ee). Copyright

Acid-Catalysed Conversion of Carbohydrates into Furan-Type Molecules in Zinc Chloride Hydrate

Acid-catalysed conversion of biomass, specifically cellulose, holds promise to create value-added, renewable replacements for many petrochemical products. We investigated an unusual acid-catalysed transformation of cellulose and cellobiose in the biphasic solvent system zinc chloride hydrate (ionic liquid)/anisole. Here, furyl hydroxymethyl ketone and furfural are obtained as major products, which are valuable but less commonly formed in high yields in transformations of cellulosic substrates. We explored this chemistry in small-scale model reactions and applied the optimised methods to the conversion of cellulose in bench-scale processes. The optimum reaction system and preferred reaction conditions are defined to select for highly desirable furanoid products in the highest known yields (up to 46 %) directly from cellulose or cellobiose. The method avoids the use of added catalysts: the ionic solvent zinc chloride hydrate possesses the intrinsic acidity required for the hydrolysis and chemical transformation steps. The process involves inexpensive media for the catalytic conversion of cellulose into high-value products under mild processing conditions.

Production of 2-hydroxyacetylfuran from lignocellulosics treated with ionic liquid-water mixtures

Japanese cedar (Cryptomeria japonica) was treated with 12 ionic liquid (IL)-water mixtures at 120 °C for 1 h. Production of 5-hydroxymethylfurfural, furfural and 2-hydroxyacetylfuran (2-HAF) was observed by HPLC and GC-MS. This is the first report to identify 2-HAF from lignocellulosics using ILs. The optimal IL-water mixture was found to be a 90% pyridinium chloride and 10% water w/w solution, although any IL-water mixture that contained pyridinium or imidazolium salts produced all three compounds in varying yields.

A new chemical synthesis of Ascopyrone P from 1,5-anhydro-d-fructose

The naturally occurring antioxidant Ascopyrone P (1,5-anhydro-4-deoxy-d-glycero-hex-1-en-3-ulose, 1) was prepared from the rare sugar 1,5-anhydro-d-fructose (AF, 3) in three steps in an overall yield of 36%. Thus, acetylation of 3 afforded the enolone 3,6-di-O-acetyl-1,5-anhydro-4-deoxy-d-glycero-hex-3-en-2-ulopyranose (4), which could be isomerised to 2,6-di-O-acetyl-1,5-anhydro-4-deoxy-d-glycero-hex-1-ene-3-ulose (6). Deacetylation of 6 under mild conditions gave crystalline Ascopyrone P (1).

Chiral Bidentate Phosphoramidite-Pd Catalyzed Asymmetric Decarboxylative Dipolar Cycloaddition for Multistereogenic Tetrahydrofurans with Cyclic N-Sulfonyl Ketimine Moieties

An asymmetric [3 + 2] cycloaddition of vinyl ethylenecarbonates (VECs) and (E)-3-arylvinyl substituted benzo[d] isothiazole 1,1-dioxides has been developed using the Pd complex of a bidentate phosphoramidite (Me-BIPAM) as the catalyst, providing a wide variety of chiral multistereogenic vinyltetrahydrofurans in good yields with excellent diastereo- and enantioselectivities (up to >20:1 dr, 99% ee).

Preparation and Application of α-Imino Ketones through One-Pot Tandem Reactions Based on Heyns Rearrangement

α-Imino ketone is a useful building block for the preparation of α-amino ketones and α-amino alcohols. However, its preparation has been seldomly seen. Herein, a metal-free and operationally simple strategy has been developed to generate α-imino ketones with high regioselectivity. Meanwhile, the method allowed for the preparation of various N,O-ketals with high regioselectivities and diastereoselectivities through cascade reactions in one pot.

Asymmetric synthesis of 7-aza-phomopsolide E and its C-4 epimer

A flexible, enantioselective route to highly functionalized α,β-unsaturated δ-lactones has been applied to the synthesis of 7-aza-phomopsolide E and its C-4 epimer. This approach relies on the application of the Noyori asymmetric hydrogenation of furyl ketone to produce the secondary furyl alcohol in high enantioexcess, which can be stereoselectively transformed into α,β-unsaturated-δ-lactones by a short, highly diastereoselective oxidation and reduction sequence. DCC and acid chloride couplings were used to introduce the side chains of the two natural product analogues.

Enantioselective [3 + 2] Cycloaddition Reaction of Ethynylethylene Carbonates with Malononitrile Enabled by Organo/Metal Cooperative Catalysis

The first catalytic asymmetric decarboxylative [3 + 2] cycloaddition reaction of ethynylethylene carbonates with malononitrile has been developed successfully by an organo/copper cooperative system. This strategy led to a series of optically active polysu

Direct Aerobic Oxidative Reactions of 2-Hydroxyacetophenones

Valuable and direct aerobic oxidation reactions of 2-hydroxyacetophenones were explored. The concept was based on the in situ treatment of small quantities of aerobically formed α-keto aldehydes that drove the reactions to the corresponding products. This new strategy was applied for a variety of oxidative reactions of 2-hydroxyacetophenones, and valuable products such as phthalides, quinoxalines, and α-keto amides were obtained in good to high yields.