6270-56-0

Basic information

• Product Name: 2-(ETHOXYMETHYL)FURAN
• Synonyms: FEMA 4114;FURFURYL ETHYL ETHER;2-(ETHOXYMETHYL)FURAN;Ai3-23507;Einecs 228-454-7;Furan, 2-(ethoxymethyl)-;2-(ethoxymethyl)-fura;ETHYL FURFURYL ETHER
• CAS NO: 6270-56-0
• Molecular Formula: C₇H₁₀O₂
• Molecular Weight: 126.15
• EINECS: 228-454-7
• Mol File: 6270-56-0.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 194.28°C (rough estimate)
• Flash Point: 41.2 °C
• Appearance: /
• Density: 0.9906
• Vapor Pressure: 9.11mmHg at 25°C
• Refractive Index: 1.4523
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-(ETHOXYMETHYL)FURAN(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(ETHOXYMETHYL)FURAN(6270-56-0)
• EPA Substance Registry System: 2-(ETHOXYMETHYL)FURAN(6270-56-0)

Safety Data

• Hazardous Substances Data: 6270-56-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H10O2/c1-2-8-6-7-4-3-5-9-7/h3-5H,2,6H2,1H3

Synthetic route

(2-furyl)methyl alcohol (98-00-0) + ethanol (64-17-5) → 2-(ethoxymethyl)furan (6270-56-0)

Conditions	Yield
With tin(IV) oxide at 200℃; for 20h; Temperature; Reagent/catalyst;	95%
With arenesulfonic acid and phenyl groups functionalized ethane bridged organosilica nanohybrid at 120℃; for 0.5h; Reagent/catalyst; Autoclave;
With Zr-mesoporous silica (SBA-15) at 100℃; for 5h;
With niobium pentoxide nanowires calcined at 100 ∘C at 100℃; under 6000.6 Torr; for 5h;

(2-furyl)methyl alcohol (98-00-0) + ethanol (64-17-5) → 2-(ethoxymethyl)furan (6270-56-0) + 4,5,5-triethoxypentan-2-one (1446756-00-8) + 4-oxopentanoic acid ethyl ester (539-88-8)

Conditions	Yield
at 110℃; for 2h; Temperature; Reagent/catalyst; Autoclave; Ionic liquid;	A n/a B n/a C 92%
With hydrothermally treated graphene oxide (GO-HT) at 120℃; for 6h; Autoclave;	A 38.8% B 11.7% C 39.7%

(2-furyl)methyl alcohol (98-00-0) + ethanol (64-17-5) → 2-(ethoxymethyl)furan (6270-56-0) + 4-oxopentanoic acid ethyl ester (539-88-8)

Conditions	Yield
With sulfonic acid-functionalized MIL-101(Cr) at 140℃; for 2h; Temperature; Reagent/catalyst; Autoclave;	A n/a B 79.2%
With hierarchical-HZ-5 at 99.84℃; for 4h; Catalytic behavior; Green chemistry;	A 26% B 73%
With hierarchical-HZ-5 at 99.84℃; for 4h; Catalytic behavior; Green chemistry;	A 49% B 41%

2-(diethoxymethyl)furan (13529-27-6) → furfural (98-01-1) + 2-(ethoxymethyl)furan (6270-56-0) + Ethyl 2-furoate (614-99-3)

Conditions	Yield
With boron trifluoride diethyl etherate In 1,2-dichloro-ethane at 0℃; for 0.25h;	A 19% B 54% C 15%
With boron trifluoride diethyl etherate In 1,2-dichloro-ethane at 0℃; for 0.25h; Mechanism;	A 19% B 54% C 15%
monoaluminum phosphate at 150℃; Product distribution; other catalysts ( γ-alumina, γ-aluminium sulphate), other temperatures, other (substituted) furaldehyde acetals;

(2-furyl)methyl alcohol (98-00-0) + ethanol (64-17-5) → 2-(ethoxymethyl)furan (6270-56-0) + 2-(diethoxymethyl)furan (13529-27-6) + 4-oxopentanoic acid ethyl ester (539-88-8)

Conditions	Yield
With silica-supported nickel phosphide at 180℃; under 750.075 Torr; for 3h; Temperature; Inert atmosphere; Autoclave;	A 53.7% B 7.4% C 35.3%

(2-furyl)methyl alcohol (98-00-0) + ethanol (64-17-5) → 2-(ethoxymethyl)furan (6270-56-0) + 4,5,5-triethoxypentan-2-one (1446756-00-8)

Conditions	Yield
With graphene oxide at 80℃; for 6h; Autoclave;	A 22.2% B 12.3%

2-Chloromethylfuran (617-88-9) + ethanol (64-17-5) → 2-(ethoxymethyl)furan (6270-56-0)

Conditions	Yield
With potassium hydroxide; diethyl ether at 75 - 80℃;

2-(Iodomethyl)tetrahydrofuran (117680-17-8) + ethanol (64-17-5) → 2-(ethoxymethyl)furan (6270-56-0)

Conditions	Yield
With potassium hydroxide; diethyl ether

(2-furyl)methyl alcohol (98-00-0) + ethyl iodide (75-03-6) → 2-(ethoxymethyl)furan (6270-56-0)

Conditions	Yield
With potassium hydroxide

tri-n-butyl-tin hydride (688-73-3) + 2-(furan-2-yl)-1,3-oxathiolane (81932-19-6) → 2-(ethoxymethyl)furan (6270-56-0) + C19H36O2SSn (127084-52-0)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In benzene Product distribution; Heating;

(2-furyl)methyl alcohol (98-00-0) → 2-(ethoxymethyl)furan (6270-56-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: absolute diethyl ether; phosphorus triiodide 2: KOH-solution; diethyl ether View Scheme
Multi-step reaction with 2 steps 1: pyridine; diethyl ether; thionyl chloride 2: KOH-solution; diethyl ether / 75 - 80 °C View Scheme

furfural (98-01-1) + ethanol (64-17-5) → furan (110-00-9) + 2-methylfuran (534-22-5) + (2-furyl)methyl alcohol (98-00-0) + 2-(ethoxymethyl)furan (6270-56-0) + furan 2-(2-furanylmethyl)-5-methyl

Conditions	Yield
With Ru/RuO2/C; hydrogen at 180℃; for 5h; Inert atmosphere;

(2-furyl)methyl alcohol (98-00-0) + ethanol (64-17-5) → 2-(ethoxymethyl)furan (6270-56-0) + diethyl ether (60-29-7) + 4,5,5-triethoxypentan-2-one (1446756-00-8) + 4-oxopentanoic acid ethyl ester (539-88-8)

Conditions	Yield
With hierarchical-HZ-5 at 99.84℃; for 2h; Catalytic behavior; Green chemistry;

(2-furyl)methyl alcohol (98-00-0) + ethanol (64-17-5) → 2-(ethoxymethyl)furan (6270-56-0) + 4,5-diethoxy-5-hydroxypentan-2-one + 4-oxopentanoic acid ethyl ester (539-88-8)

Conditions	Yield
With 12.1PW12/ZrO2 bifunctionalized organosilica nanotubes at 120℃; Autoclave; High pressure;

(2-furyl)methyl alcohol (98-00-0) + ethanol (64-17-5) → 5-methyl-5H-furan-2-one (591-11-7) + 5-methyl-2-furanone (591-12-8) + 2-(ethoxymethyl)furan (6270-56-0) + 4-oxopentanoic acid ethyl ester (539-88-8)

Conditions	Yield
With zeolite H-beta at 110℃; for 1.5h; Autoclave;	A n/a B n/a C 14.4 %Chromat. D 23.3 %Chromat.

furfural (98-01-1) + ethanol (64-17-5) → (2-furyl)methyl alcohol (98-00-0) + 2-(ethoxymethyl)furan (6270-56-0)

Conditions	Yield
With formic acid at 100℃; for 5h; Sealed tube;
With hydrogen at 60℃; under 2250.23 Torr; for 2h; Catalytic behavior; Pressure;

furfural (98-01-1) + ethanol (64-17-5) → 2-methyltetrahydrofuran (96-47-9) + Tetrahydrofurfuryl alcohol (97-99-4) + (2-furyl)methyl alcohol (98-00-0) + 2-(ethoxymethyl)furan (6270-56-0) + 2-(diethoxymethyl)tetrahydrofuran (90755-37-6)

Conditions	Yield
With hydrogen at 80℃; under 3750.38 Torr; for 2h;

furfural (98-01-1) + ethanol (64-17-5) → Tetrahydrofurfuryl alcohol (97-99-4) + (2-furyl)methyl alcohol (98-00-0) + 2-(ethoxymethyl)furan (6270-56-0)

Conditions	Yield
With hydrogen at 60℃; under 2250.23 Torr; for 2h; Reagent/catalyst;

furfural (98-01-1) + ethanol (64-17-5) → 2-(ethoxymethyl)furan (6270-56-0) + 2-(diethoxymethyl)furan (13529-27-6)

Conditions	Yield
With hydrogen at 60℃; under 750.075 Torr; for 2h;

furfural (98-01-1) + ethanol (64-17-5) → 2-(ethoxymethyl)furan (6270-56-0) + 2-(diethoxymethyl)furan (13529-27-6) + 2-(diethoxymethyl)tetrahydrofuran (90755-37-6)

Conditions	Yield
With hydrogen at 60℃; under 2250.23 Torr; for 2h;

furfural (98-01-1) + ethanol (64-17-5) → (2-furyl)methyl alcohol (98-00-0) + 2-(ethoxymethyl)furan (6270-56-0) + 2-(diethoxymethyl)furan (13529-27-6)

Conditions	Yield
With hydrogen at 60℃; under 2250.23 Torr; for 2h; Reagent/catalyst; Temperature; Pressure;

furfural (98-01-1) + ethanol (64-17-5) → (2-furyl)methyl alcohol (98-00-0) + 2-(ethoxymethyl)furan (6270-56-0) + 2-(diethoxymethyl)tetrahydrofuran (90755-37-6)

Conditions	Yield
With hydrogen at 60℃; under 2250.23 Torr; for 2h;

2-(diethoxymethyl)furan (13529-27-6) → (2-furyl)methyl alcohol (98-00-0) + 2-(ethoxymethyl)furan (6270-56-0) + 2-(diethoxymethyl)tetrahydrofuran (90755-37-6)

Conditions	Yield
With hydrogen In ethanol at 60℃; under 2250.23 Torr; for 2h;

furfural (98-01-1) → 2-(ethoxymethyl)furan (6270-56-0) + 2-(diethoxymethyl)tetrahydrofuran (90755-37-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen; / 2 h / 60 °C / 2250.23 Torr 2: hydrogen; / ethanol / 2 h / 60 °C / 2250.23 Torr View Scheme
Multi-step reaction with 2 steps 1: hydrogen; / 2 h / 60 °C / 750.08 Torr 2: hydrogen; / ethanol / 2 h / 60 °C / 2250.23 Torr View Scheme
Multi-step reaction with 2 steps 1: hydrogen; / 2 h / 60 °C / 2250.23 Torr 2: hydrogen; / ethanol / 2 h / 60 °C / 2250.23 Torr View Scheme
Multi-step reaction with 2 steps 1: hydrogen; / 2 h / 60 °C / 2250.23 Torr 2: hydrogen; / ethanol / 2 h / 60 °C / 2250.23 Torr View Scheme

(2-furyl)methyl alcohol (98-00-0) + ethanol (64-17-5) → 5-methyl-2-furanone (591-12-8) + 2-(ethoxymethyl)furan (6270-56-0) + 2,2'-difurylmethane (1197-40-6) + 4-oxopentanoic acid ethyl ester (539-88-8)

Conditions	Yield
With niobium pentoxide nanowires calcined at 100 ∘C at 160℃; under 6000.6 Torr; for 5h; Temperature;

(2-furyl)methyl alcohol (98-00-0) + ethanol (64-17-5) → 5-methyl-2-furanone (591-12-8) + 2-(ethoxymethyl)furan (6270-56-0)

Conditions	Yield
With niobium pentoxide nanowires calcined at 100 ∘C at 120℃; under 6000.6 Torr; for 5h;

2-(ethoxymethyl)furan (6270-56-0) → furfural (98-01-1)

Conditions	Yield
With water; 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate In acetonitrile at 20℃; for 8h;	90%

2-(ethoxymethyl)furan (6270-56-0) + dimethyl acetylenedicarboxylate (762-42-5) → dimethyl 4-(ethoxymethyl)-7-oxabicyclo [2.2.1] hepta-2,5-diene-2,3-dicarboxylate

Conditions	Yield
In toluene at 100℃; for 16h; Sealed tube;	64%

2-(ethoxymethyl)furan (6270-56-0) + butan-1-ol (71-36-3) → butyl levulinate (2052-15-5)

Conditions	Yield
With bismuth(lll) trifluoromethanesulfonate In water at 117℃; for 2.75h; Concentration;	53%

2-(ethoxymethyl)furan (6270-56-0) + formaldehyd (50-00-0) → (5-(ethoxymethyl)furan-2-yl)methanol (113983-97-4)

Conditions	Yield
With acetic acid at 70 - 80℃; for 3h;	46%

2-(ethoxymethyl)furan (6270-56-0) + dimethyl acetylenedicarboxylate (762-42-5) → dimethyl 3-(ethoxymethyl)-6-hydroxy-1,2-benzenedicarboxylate

Conditions	Yield
Stage #1: dimethyl acetylenedicarboxylate With scandium tris(trifluoromethanesulfonate) In acetonitrile at 20℃; for 0.166667h; Stage #2: 2-(ethoxymethyl)furan In acetonitrile at 100℃; for 16h; Sealed tube;	32%

2-(ethoxymethyl)furan (6270-56-0) → C7H9(2)HO2 + C7H9(2)HO2 + C7H9(2)HO2

Conditions	Yield
With sodium methylate In deuteromethanol; toluene at 85℃; for 2h; Product distribution; Heating; other temperature;	A 5% B 16% C 27%

2-(ethoxymethyl)furan (6270-56-0) + chloro-trimethyl-silane (75-77-4) → 2-ethoxymethyl-5-trimethylsilylfuran (93271-55-7)

Conditions	Yield
With n-butyllithium 1)ether in ether,0 deg C, 5 min 2)trimethylchlorosilane, -70 deg C, 30 min 3)room temp. 30 min; Yield given. Multistep reaction;

2-(ethoxymethyl)furan (6270-56-0) + pentachlorocyclopropane (6262-51-7) → (1S*,5S*)-2,3,4,4-tetrachloro-1-ethoxymethyl-8-oxabicyclo-[3.2.1]octa-2,6-diene (1160560-98-4)

Conditions	Yield
Stage #1: pentachlorocyclopropane With potassium hydroxide In 1,4-dioxane at 20 - 65℃; for 1h; Stage #2: 2-(ethoxymethyl)furan In 1,4-dioxane at 85 - 90℃; for 16h;

2-(ethoxymethyl)furan (6270-56-0) + 5-(ethoxymethyl)furfural (1917-65-3) → (5-(ethoxymethyl)furan-2-yl)methanol (113983-97-4)

Conditions	Yield
With hydrogen; Pd on active carbon
With hydrogen

maleic anhydride (108-31-6) + 2-(ethoxymethyl)furan (6270-56-0) → 1-ethoxymethyl-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride (1428945-27-0)

Conditions	Yield
at 20℃; for 36h;
In neat (no solvent) at 15 - 20℃; for 26h; Diels-Alder Cycloaddition;

2-(ethoxymethyl)furan (6270-56-0) → 3-(ethoxymethyl)phthalic acid disodium salt

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 36 h / 20 °C 2.1: sodium methylate / methanol / 18 h / 0 - 20 °C 2.2: 5 h / Reflux View Scheme

2-(ethoxymethyl)furan (6270-56-0) → benzene-1,2,3-tricarboxlic acid (569-51-7)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 36 h / 20 °C 2.1: sodium methylate / methanol / 18 h / 0 - 20 °C 2.2: 5 h / Reflux 3.1: potassium permanganate / water / 18 h / 20 °C View Scheme

2-(ethoxymethyl)furan (6270-56-0) + isopropyl alcohol (67-63-0) → 5-methyl-5H-furan-2-one (591-11-7) + 5-methyl-2-furanone (591-12-8) + isopropyl levulinate (21884-26-4) + levulinic acid (123-76-2)

Conditions	Yield
With zeolite H-beta at 110℃; for 1.5h; Autoclave;	A n/a B n/a C 7.7 %Chromat. D 6.4 %Chromat.

Upstream product

• 617-88-9 2-Chloromethylfuran 
• 64-17-5 ethanol 
• 117680-17-8 2-(Iodomethyl)tetrahydrofuran 
• 98-00-0 (2-furyl)methyl alcohol 
• 75-03-6 ethyl iodide 
• 98-01-1 furfural 
• 13529-27-6 2-(diethoxymethyl)furan 
• 688-73-3 tri-n-butyl-tin hydride 
• 81932-19-6 2-(furan-2-yl)-1,3-oxathiolane 

Downstream Products

• 591-11-7 5-methyl-5H-furan-2-one 
• 591-12-8 5-methyl-2-furanone 
• 21884-26-4 isopropyl levulinate 
• 123-76-2 levulinic acid 
• 96-47-9 2-methyltetrahydrofuran 
• 62435-71-6 2-(ethoxymethyl)tetrahydrofuran 
• 108-29-2 5-methyl-dihydro-furan-2-one 
• 1016708-78-3 2-(ethoxymethyl)benzonitrile 
• 861519-73-5 3-(ethoxymethyl)benzonitrile 
• 2052-15-5 butyl levulinate 
• 539-88-8 4-oxopentanoic acid ethyl ester 
• 569-51-7 benzene-1,2,3-tricarboxlic acid 
• 98-01-1 furfural 

Relevant articles and documents

Utilization of renewable resources: Investigation on role of active sites in zeolite catalyst for transformation of furfuryl alcohol into alkyl levulinate

A bio-derived furfuryl alcohol transformation into various high-value chemicals is a growing field of interest among researchers. This study reports an exclusive investigation of the porosity and active sites responsible for the efficient alcoholysis of furfuryl alcohol to alkyl levulinate by the aid of zeolite catalyst. Alkyl levulinate is a promising platform chemical potentially used as a fuel additive and also for the production of chemicals. A detailed study using well-characterized HZSM-5 catalyst on the influence of acidity and post synthesis modification like desilication, dealumination, metal ion exchange and phosphate modification revealed the most desired type of acid sites required to catalyze this reaction. Among the HZSM-5 catalysts tested, HZSM-5 (SAR 95) showed the best performance of ≥ 99 % furfuryl alcohol conversion and 85 % butyl levulinate selectivity under optimum conditions. The catalyst exhibited good recyclability additionally addressing all the challenges reported in the previous literature fulfilling the green chemistry principles.

Etherification of biomass-derived furanyl alcohols with aliphatic alcohols over silica-supported nickel phosphide catalysts: Effect of surplus P species on the acidity

The acidity of nickel phosphide (Ni2P) catalysts plays a crucial role in producing a desired hydrodeoxygenation molecule from biomass-derived substrates; yet, it has never been explored in acid-catalyzed reactions. Herein, we demonstrated the activity of silica-supported Ni2P catalyst prepared with the nominal P/Ni ratio of 2 (Ni2P/SiO2-2P) in the etherification of furanyl alcohols (particularly, 5-(hydroxymethyl)furfural) with aliphatic alcohols including ethanol. By comparing the characteristics of Ni/SiO2, PxOy/SiO2, and Ni2P/SiO2-xP (x = 0.5 and 1), Ni2P/SiO2-2P was revealed to contain the Br?nsted and Lewis acid sites of which both contributed to the etherification reaction. Notably, the Br?nsted acidity was associated with the surplus P species added to produce the Ni2P phase. Consequently, supported Ni2P catalysts can work in acid-catalyzed reactions if an adequate ratio of Br?nsted to Lewis acid sites is provided by the amount of the surplus P species determined by adjusting the P/Ni ratio.

SINGLE STEP PROCESS FOR THE SYNTHESIS OF FURFURYL ETHYL ETHER

The present invention provides a single step process for the synthesis of furfuryl ethyl ether comprises refluxing the reaction mixture of furfuryl alcohol, ethanol and catalyst at temperature in the range of 80 to 120° C. for the period in the range of 3 to 7 hrs to afford furfuryl ethyl ether. The catalyst used in present invention is Zr incorporated SBA-15. Further, the conversion of furfuryl alcohol is in the range of 60 to 90%. The selectivity of reaction towards furfuryl ethyl ether is in the range of 85 to 95%.