97-99-4

Basic information

• Product Name: Tetrahydrofurfuryl alcohol
• Synonyms: TETRAHYDROFURFURYL ALCOHOL FCC;tetrahydro-2-furylmethanol tetrahydrofurfuryl alcohol;2-Hydroxymethyl oxolane;2-Oxolanemethanol;Oxolane-2-methanol;Tetrahydrofuran-2-methanol;Tetrahydrofurfruyl Alcohol;Tetrahydrofurfuryl a
• CAS NO: 97-99-4
• Molecular Formula: C₅H₁₀O₂
• Molecular Weight: 102.13
• EINECS: 202-625-6
• Product Categories: Building Blocks;C4 to C7;Chemical Synthesis;Heterocyclic Building Blocks;fine chemical;Solvent for fats, waxes, resins, in organic synthesis.;Pharmaceutical intermediates;Furan&Benzofuran;Furans
• Mol File: 97-99-4.mol
• Article Data: 282

Chemical Properties

• Melting Point: -80 °C
• Boiling Point: 178 °C(lit.)
• Flash Point: 183 °F
• Appearance: Clear/Liquid
• Density: 1.0543
• Vapor Density: 3.52 (vs air)
• Vapor Pressure: 2.3 mm Hg ( 39 °C)
• Refractive Index: n20/D 1.452(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: acetone: miscible(lit.)
• PKA: 14.44±0.10(Predicted)
• Explosive Limit: 1.5-9.7%(V)
• Water Solubility: soluble
• Sensitive: Hygroscopic
• Merck: 14,9213
• BRN: 102723
• CAS DataBase Reference: Tetrahydrofurfuryl alcohol(CAS DataBase Reference)
• NIST Chemistry Reference: Tetrahydrofurfuryl alcohol(97-99-4)
• EPA Substance Registry System: Tetrahydrofurfuryl alcohol(97-99-4)

Safety Data

• Hazard Codes: Xi,T
• Statements: 36-62-61
• Safety Statements: 39-36/37/39
• RIDADR: NA 1993 / PGIII
• WGK Germany: 2
• RTECS: LU2450000
• TSCA: Yes
• Hazardous Substances Data: 97-99-4(Hazardous Substances Data)

Usage

Preparation

By catalytic reduction of furfural with Raney-Ni; also by destructive hydrogenation of lignin.

Chemical Properties

Colorless to light yellow liqui

Uses

Solvent for vinyl resins; dyes for leather; chlorinated rubber; cellulose esters; solvent softener for nylon; vegetable oils; coupling agent; organic synthesis.

General Description

A clear colorless liquid with a mild odor. Flash point 167°F. Vapors are heavier than air.

Air & Water Reactions

Denser than water and soluble in water.

Health Hazard

Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Reactivity Profile

Acetyl bromide reacts violently with alcohols or water [Merck 11th ed. 1989]. Mixtures of alcohols with concentrated sulfuric acid and strong hydrogen peroxide can cause explosions. Example: An explosion will occur if dimethylbenzylcarbinol is added to 90% hydrogen peroxide then acidified with concentrated sulfuric acid. Mixtures of ethyl alcohol with concentrated hydrogen peroxide form powerful explosives. Mixtures of hydrogen peroxide and 1-phenyl-2-methyl propyl alcohol tend to explode if acidified with 70% sulfuric acid [Chem. Eng. News 45(43):73. 1967; J, Org. Chem. 28:1893. 1963]. Alkyl hypochlorites are violently explosive. They are readily obtained by reacting hypochlorous acid and alcohols either in aqueous solution or mixed aqueous- carbon tetrachloride solutions. Chlorine plus alcohols would similarly yield alkyl hypochlorites. They decompose in the cold and explode on exposure to sunlight or heat. Tertiary hypochlorites are less unstable than secondary or primary hypochlorites [NFPA 491 M 1991]. Base-catalysed reactions of isocyanates with alcohols should be carried out in inert solvents. Such reactions in the absence of solvents often occur with explosive violence [Wischmeyer 1969].

Occurrence

Reported found in shoyu (fermented soya hydrolysate), coffee and fresh mango.

Chemical Properties

Tetrahydrofurfuryl alcohol has a faint, warm, oily, caramellic odor with a coffee and nut-like flavor at very low levels (0.03 to 1 ppm).

Carcinogenicity

Tetrahydro-2-furanmethanol was not mutagenic to S. typhimurium strains TA100, TA1535, TA1537, or TA98 in an in vitro gene mutation assay or to E. coliWP2uvrA/pKM101 with or withoutmetabolic activation. No chromosomal aberrations or polypoidy were observed when tetrahydro-2-furanmethanol was added to cultured Chinese hamster lung cells with or without metabolic activation .

InChI:InChI=1/C5H10O2/c6-4-5-2-1-3-7-5/h5-6H,1-4H2

Synthetic route

furfural (98-01-1) → Tetrahydrofurfuryl alcohol (97-99-4)

Conditions	Yield
With hydrogen In ethanol at 60℃; under 15001.5 Torr; for 4h; Catalytic behavior; Reagent/catalyst; Temperature; Solvent; Pressure; Autoclave; Green chemistry;	100%
With hydrogen In butan-1-ol at 80℃; under 30003 Torr; for 5h; Catalytic behavior; Temperature; Reagent/catalyst;	99%
With hydrogen In isopropyl alcohol at 179.84℃; under 22502.3 Torr; for 1.25h; Reagent/catalyst;	99%

(2-furyl)methyl alcohol (98-00-0) → Tetrahydrofurfuryl alcohol (97-99-4)

Conditions	Yield
With 3% Pd/C; hydrogen In isopropyl alcohol at 219.84℃; under 25858.1 Torr; for 5h; Inert atmosphere;	100%
With hydrogen In isopropyl alcohol at 25℃; under 7500.75 Torr; for 3h; Green chemistry;	100%
With palladium on activated charcoal; ammonia; hydrogen In tetrahydrofuran at 160℃; for 4h; Reagent/catalyst; Autoclave;	100%

5-hydroxy-1,2-epoxypentane (21915-56-0) → Tetrahydrofurfuryl alcohol (97-99-4)

Conditions	Yield
With Hexafluorobenzene at 20℃; for 22h;	100%
With C10H12NO(1+)*BF4(1-) In dichloromethane
With hydrogenchloride In water; tert-butyl alcohol at 20℃; for 2h; Green chemistry;
With Hexafluorobenzene In dichloromethane-d2 at 20℃; Kinetics; Reagent/catalyst; Solvent;

n-Pent-4-enyl alcohol (821-09-0) → Tetrahydrofurfuryl alcohol (97-99-4)

Conditions	Yield
With pyridine-3-carbonitrile; dihydrogen peroxide; methyltrioxorhenium(VII) In dichloromethane at 24℃; for 18h;	97%
With C10H12NO(1+)*BF4(1-) In dichloromethane for 3.5h; Ambient temperature;	95%
With molecular sieve; dihydrogen peroxide In water at 59.85℃; for 3h;	99 % Chromat.

tetrahydrofurfuryl acetate (637-64-9) → Tetrahydrofurfuryl alcohol (97-99-4)

Conditions	Yield
With ytterbium(III) triflate In isopropyl alcohol for 8h; Deacetylation; Heating;	95%
With MetProLeuAspGlnProThrAlaAlaPheLeuAspPheLeuArgSerSerGlyGlyLysProLeuTyrGluLeuProLeuAlaGluAlaArgAlaAlaMetAlaMetGlySerGlnLeuGlyAlaProProAlaAspValGlyArgIleValAspArgSerIleAspValProGlyGlyAlaValAlaLeuArgIleTyrThrProAlaThrThrLysAlaGlyGlyLeuLeuProAlaIleLeuGlnTyrHisGlyGlyGlyPheValLeuGlyAsnLeuAspThrHisGluSerIleAlaArgPheTyrCysAlaHisAlaGlyAlaValValIleSerValAspTyrArgLeuAlaProGluHisArgPheProThrGlnValGluAspSerPheAlaAlaLeuThrTrpValSerGluHisAlaSerGluLeuGlyValAspProAlaArgValAlaValAlaGlyAspSerAlaGlyGlyAsnLeuAlaThrValMetCysLeuLeuAlaLysAlaArgGlyGlyProArgIleAlaCysGlnAlaLeuLeuTyrProValAlaAspPheArgProGluGlnValTyrAlaSerHisAlaGlnPheGlyAspGlySerTyrPheLeuSerSerLysAspMetAspTrpPheArgAlaSerTyrPheThrAspValAlaSerGlnAlaAlaGluProThrAlaSerProMetAlaThrThrAspLeuSerGlyLeuProProAlaLeuValThrThrAlaGlyCysAspProLeuLeuAspGluGlyArgAlaTyrAlaAspArgLeuLysAlaAlaGlyValProValAspTyrArgCysPheGluThrThrIleHisAlaCysAlaSerPheAlaGlyThrIleProAlaGlyLeuAspMetLeuGlyPheValAlaAspTrpLeuAlaAlaHisThrLys In aq. phosphate buffer at 37℃; pH=7.5; Reagent/catalyst; Enzymatic reaction; enantioselective reaction;

tetrahydrofurfuryl tetrahydropyranyl ether (710-14-5) → Tetrahydrofurfuryl alcohol (97-99-4)

Conditions	Yield
With methanol; zirconium(IV) chloride at 20℃; for 7h;	93%

furfural (98-01-1) → Tetrahydrofurfuryl alcohol (97-99-4) + tetrahydrofuran-2-carbaldehyde (7681-84-7)

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen In water at 2℃; under 60006 Torr; for 2h; Reagent/catalyst; Autoclave;	A 91.9% B n/a
With hydrogen In water at 1.84℃; under 60006 Torr; for 4h; Catalytic behavior; Autoclave;
With palladium on activated charcoal; hydrogen In toluene at 170℃; under 52505.3 Torr; for 1h; Solvent; Autoclave;	A 52.2%Chromat. B 7.6%Chromat.

furfural (98-01-1) → Tetrahydrofurfuryl alcohol (97-99-4) + TETRAHYDROFURFURYLAMINE (4795-29-3)

Conditions	Yield
With ammonia; hydrogen In tetrahydrofuran at 180℃; for 12h; Autoclave;	A 5.1% B 91%
Multi-step reaction with 2 steps 1: ammonia; hydrogen / tetrahydrofuran / 2 h / 80 °C / Autoclave 2: ammonia; hydrogen / tetrahydrofuran / 24 h / 160 °C / Autoclave View Scheme

furfural (98-01-1) → Tetrahydrofurfuryl alcohol (97-99-4) + (2-furyl)methyl alcohol (98-00-0)

Conditions	Yield
With hydrogen at 90℃; under 15001.5 Torr; Reagent/catalyst;	A 90.5% B 8.4%
With hydrogen In butan-1-ol at 40℃; under 30003 Torr; for 7h; Catalytic behavior; Reagent/catalyst;	A 12% B 85%
With hydrogen In tetrahydrofuran at 175℃; under 7500.75 Torr; for 8h; Catalytic behavior; Pressure; Temperature; Time; chemoselective reaction;	A 10% B 79.5%

furfural (98-01-1) → Tetrahydrofurfuryl alcohol (97-99-4) + 1,4-Pentanediol (626-95-9)

Conditions	Yield
With carbon dioxide; hydrogen In water at 80℃; under 30003 Torr; for 20h; Catalytic behavior; Reagent/catalyst; Pressure; Temperature; Autoclave;	A 9% B 90%
With hydrogen In water at 140℃; under 11251.1 Torr; for 4h; Kinetics; Temperature; Autoclave;	A 7% B 87%

2-(((4-methoxybenzyl)oxy)methyl)tetrahydrofuran (69406-23-1) → Tetrahydrofurfuryl alcohol (97-99-4)

Conditions	Yield
With 4,4'-bipyridine; (phthalocyaninato)iron(II); oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene at 80℃; under 3000.3 Torr; for 24h; Autoclave;	86%
With 4,4'-bipyridine; oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene at 120℃; under 3750.38 Torr; for 7h; Autoclave; Green chemistry;	65%
With ammonium peroxydisulfate; 9-(2-mesityl)-10-methylacridinium perchlorate In dichloromethane; water at 20 - 30℃; for 3.5h; Irradiation; Green chemistry;	65%
With tert.-butylnitrite; oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone In monoethylene glycol diethyl ether at 120℃; under 1500.15 Torr; for 1.5h;
With tert.-butylnitrite; oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone In chlorobenzene at 100℃; under 760.051 Torr; for 1h;

(2-furyl)methyl alcohol (98-00-0) → Tetrahydrofurfuryl alcohol (97-99-4) + 2-methylfuran (534-22-5)

Conditions	Yield
With hydrogen at 250℃; under 760.051 Torr;	A 6.2% B 83.3%
With hydrogen In methanol at 25℃; under 750.075 Torr; for 1h; Reagent/catalyst; Sealed tube; Green chemistry;	A 69.4% B 14.3%
With hydrogen In ethanol at 25℃; for 1h; Sealed tube; Green chemistry;	A 43% B 50%

tetrahydro-2-furancarboxylic acid (16874-33-2) → Tetrahydrofurfuryl alcohol (97-99-4)

Conditions	Yield
With hydrogen In neat (no solvent) at 160℃; under 37503.8 Torr; for 24h;	83%
Stage #1: tetrahydro-2-furancarboxylic acid With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at -20 - 20℃; Stage #2: With water In tetrahydrofuran; diethyl ether; ethyl acetate at 0 - 20℃;
With tin(II) trifluoromethanesulfonate; tris(2,4-pentanedionato)ruthenium(III); hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In water; toluene at 160℃; under 45004.5 Torr; for 24h; Autoclave;	80 %Chromat.

2-methylfuran (534-22-5) → 2-methyltetrahydrofuran (96-47-9) + Tetrahydrofurfuryl alcohol (97-99-4)

Conditions	Yield
With carbon dioxide; 5% Pd(II)/C(eggshell); hydrogen at 300℃; under 112511 Torr; Supercritical conditions;	A 82% B 6%

tert-butyldimethyl((tetrahydrofuran-2-yl)methoxy)silane (126680-80-6) → Tetrahydrofurfuryl alcohol (97-99-4)

Conditions	Yield
With zinc tetrafluoroborate In water for 5h; Ambient temperature;	80%
With Nafion-H(R); sodium iodide In methanol at 20℃; for 7h;

(2-furyl)methyl alcohol (98-00-0) → Tetrahydrofurfuryl alcohol (97-99-4) + 1,2-pentanediol (5343-92-0)

Conditions	Yield
With 5%PtO2-Al2O3; hydrogen In ethanol at 0 - 5℃; under 750.075 Torr; for 5h;	A 15% B 80%
With hydrogen; 5 % platinum dioxide on gamma-aluminum oxide In ethanol at 0 - 5℃; under 750.075 Torr; for 5h;	A n/a B 80%
With water; hydrogen at 120℃; under 22502.3 Torr; for 4h; chemoselective reaction;

furfural (98-01-1) → Tetrahydrofurfuryl alcohol (97-99-4) + Cyclopentanol (96-41-3) + cyclopentanone (120-92-3)

Conditions	Yield
With hydrogen In water at 160℃; under 30003 Torr; for 2.5h; Reagent/catalyst; Autoclave;	A n/a B n/a C 79%
With hydrogen In water at 175℃; under 60006 Torr; for 0.5h;	A 9.7 mol B n/a C n/a
With 20% Ni/Co3O4; hydrogen In water at 149.84℃; under 30003 Torr; for 6h; Reagent/catalyst; Autoclave; chemoselective reaction;

furfural (98-01-1) → 2-methyltetrahydrofuran (96-47-9) + Tetrahydrofurfuryl alcohol (97-99-4)

Conditions	Yield
Stage #1: furfural With hydrogen at 160℃; under 760.051 Torr; Flow reactor; Stage #2: With hydrogen at 130℃; under 760.051 Torr; Flow reactor;	A 13.7% B 78.2%
With hydrogen In 1,4-dioxane; isopropyl alcohol at 200℃; under 48754.9 Torr; for 6h; Reagent/catalyst;	A 36% B 45%
Multi-step reaction with 2 steps 1: isopropyl alcohol; 10% Pd/C / 7.5 h / 150 °C / Inert atmosphere 2: isopropyl alcohol; 10% Pd/C / 7.5 h / 180 °C / Inert atmosphere View Scheme

furfural (98-01-1) → Tetrahydrofurfuryl alcohol (97-99-4) + furan (110-00-9) + 2-methylfuran (534-22-5) + (2-furyl)methyl alcohol (98-00-0)

Conditions	Yield
With hydrogen In methanol at 119.84℃; under 7500.75 Torr; for 1h; Catalytic behavior; Solvent; Reagent/catalyst; Autoclave;	A 6.2% B 8.9% C 7.7% D 75.5%
With hydrogen In isopropyl alcohol at 180℃; under 15001.5 Torr; for 5h; Kinetics; Catalytic behavior; Time; Autoclave; Sealed tube;	A 13% B 22% C 54% D 8%
With hydrogen at 250℃; under 760.051 Torr;	A 10.2% B 13.5% C 38.6% D 19%

furfural (98-01-1) → Tetrahydrofurfuryl alcohol (97-99-4) + 2-methylfuran (534-22-5) + (2-furyl)methyl alcohol (98-00-0)

Conditions	Yield
With hydrogen In isopropyl alcohol at 229.84℃; under 30003 Torr; for 5h;	A 18% B 14% C 71%
With hydrogen In isopropyl alcohol at 229.84℃; under 30003 Torr; for 2h;	A 7.2% B 61% C 8%
With hydrogen at 30℃; Kinetics;

furfural (98-01-1) → 2-methyltetrahydrofuran (96-47-9) + Tetrahydrofurfuryl alcohol (97-99-4) + (2-furyl)methyl alcohol (98-00-0)

Conditions	Yield
Stage #1: furfural With hydrogen at 160℃; under 760.051 Torr; Flow reactor; Stage #2: With hydrogen at 120℃; under 760.051 Torr; Flow reactor;	A 13.1% B 70% C 9.1%
With Ni3Sn2; hydrogen In isopropyl alcohol at 20 - 179.84℃; for 12h; Autoclave;	A 5 %Chromat. B 5 %Chromat. C 91 %Chromat.
With hydrogen In isopropyl alcohol at 50℃; under 3750.38 Torr; Autoclave;

furfural (98-01-1) → Tetrahydrofurfuryl alcohol (97-99-4) + 1 ,5-pentanediol (111-29-5) + (+/-)-2-pentanol (6032-29-7) + pentan-1-ol (71-41-0)

Conditions	Yield
With hydrogen In isopropyl alcohol at 150℃; under 30003 Torr; for 8h; Temperature; Pressure; Autoclave;	A 68.7% B 24.2% C n/a D n/a

2,5-dihydrofuran (1708-29-8) + carbon monoxide (201230-82-2) → Tetrahydrofurfuryl alcohol (97-99-4) + 3-tetrahydrofuranmethanol (124391-75-9, 124506-31-6, 15833-61-1)

Conditions	Yield
With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); 2-(dicyclohexylphosphanyl)-1-(2-methoxyphenyl)-1H-imidazole; hydrogen In toluene at 160℃; under 37503.8 Torr; for 24h; Autoclave; Inert atmosphere; Overall yield = 60 %Chromat.; regioselective reaction;	A n/a B 66%

2,3-dihydro-2H-furan (1191-99-7) + carbon monoxide (201230-82-2) → Tetrahydrofurfuryl alcohol (97-99-4) + 3-tetrahydrofuranmethanol (124391-75-9, 124506-31-6, 15833-61-1)

Conditions	Yield
With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); 2-(dicyclohexylphosphanyl)-1-(2-methoxyphenyl)-1H-imidazole; hydrogen In toluene at 160℃; under 37503.8 Torr; for 24h; Autoclave; Inert atmosphere; Overall yield = 60 %Chromat.; regioselective reaction;	A n/a B 66%

(2-furyl)methyl alcohol (98-00-0) + methanol (67-56-1) → Tetrahydrofurfuryl alcohol (97-99-4) + methyl tetrahydrofurfuryl ether (19354-27-9) + O-methyl-pentamethylene glycol (4799-62-6)

Conditions	Yield
With palladium on activated charcoal; hydrogen at 170℃; under 52505.3 Torr; for 2h; Autoclave;	A 64.5% B n/a C n/a

(2-furyl)methyl alcohol (98-00-0) → Tetrahydrofurfuryl alcohol (97-99-4) + 1,4-Pentanediol (626-95-9) + 5-methyl-dihydro-furan-2-one (108-29-2)

Conditions	Yield
With palladium on activated charcoal; water; hydrogen at 170℃; under 52505.3 Torr; for 2h; Autoclave;	A 64% B n/a C n/a

methanol (67-56-1) + 5-hydroxymethyl-2-furfuraldehyde (67-47-0) → Tetrahydrofurfuryl alcohol (97-99-4) + methyl tetrahydrofurfuryl ether (19354-27-9) + O-methyl-pentamethylene glycol (4799-62-6)

Conditions	Yield
With palladium on activated charcoal; hydrogen at 170℃; under 52505.3 Torr; for 2h; Autoclave;	A 63.4% B n/a C n/a

furfural (98-01-1) → Tetrahydrofurfuryl alcohol (97-99-4) + 1,4-Pentanediol (626-95-9) + 5-Hydroxy-2-pentanone (1071-73-4)

Conditions	Yield
With hydrogen; toluene-4-sulfonic acid In water at 140℃; under 11251.1 Torr; for 4h; Autoclave;	A 19% B 63% C 8%
With carbon dioxide; hydrogen In water at 80℃; under 30003 Torr; for 20h; Catalytic behavior; Reagent/catalyst; Temperature; Autoclave;	A 8% B 57% C 15%

furfural (98-01-1) → Tetrahydrofurfuryl alcohol (97-99-4) + (2-furyl)methyl alcohol (98-00-0) + 2-furaldehyde dimethyl acetal (1453-62-9)

Conditions	Yield
With hydrogen In methanol at 100℃; under 15001.5 Torr; Catalytic behavior; Reagent/catalyst; Autoclave;	A n/a B 60% C n/a

furfural (98-01-1) → Tetrahydrofurfuryl alcohol (97-99-4) + furan (110-00-9) + (2-furyl)methyl alcohol (98-00-0)

Conditions	Yield
With MnO2#dotPd; hydrogen In isopropyl alcohol at 180℃; under 15001.5 Torr; for 5h; Kinetics; Catalytic behavior; Time; Autoclave; Sealed tube;	A 8.3% B 14.11% C 59.76%
With hydrogen In isopropyl alcohol at 120℃; under 45004.5 Torr; for 3h; Reagent/catalyst;
With Ni-doped silica; hydrogen at 140℃; under 760.051 Torr; for 2h; Flow reactor;

Tetrahydrofurfuryl alcohol (97-99-4) + p-toluenesulfonyl chloride (98-59-9) → rac-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate (34583-63-6)

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 1h;	100%
With potassium hydroxide	93%
With potassium iodide; silver(l) oxide In dichloromethane at 40℃;	91%

Tetrahydrofurfuryl alcohol (97-99-4) + 3-(diphenylphosphono)-2-(N-cyanoimino)thiazolidine (449813-82-5) → <(tetrahydrofurfuryl)oxy>diphenyphosphine (33026-82-3)

Conditions	Yield
With tert-butylmagnesium chloride In tetrahydrofuran at 20℃; for 0.5h; Product distribution; Further Variations:; Reagents; reaction times;	100%

Tetrahydrofurfuryl alcohol (97-99-4) + but-3-enoic acid (625-38-7) → tetrahydrofurfuryl vinylacetate (1198472-55-7)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; Inert atmosphere;	100%

Tetrahydrofurfuryl alcohol (97-99-4) + titanium(IV) isopropylate (546-68-9) → C16H32O6Ti (1346523-06-5)

Conditions	Yield
In cyclohexane Inert atmosphere; Reflux;	100%
In cyclohexane for 0.5h; Schlenk technique; Inert atmosphere; Reflux;	100%

Tetrahydrofurfuryl alcohol (97-99-4) + 3,4-dihydro-2H-pyran (110-87-2) → tetrahydrofurfuryl tetrahydropyranyl ether (710-14-5)

Conditions	Yield
With zirconium(IV) chloride In dichloromethane for 3h;	99%
With Envirocat EPZG at 0 - 5℃; for 1h;	98%
With 1-butyl-3-methylimidazolium hydrogen sulfate at 20℃; for 0.166667h;	98%

Tetrahydrofurfuryl alcohol (97-99-4) + acetic anhydride (108-24-7) → tetrahydrofurfuryl acetate (637-64-9)

Conditions	Yield
With phosphoric acid In acetonitrile at 50℃; for 3h;	99%
With zirconium sulfophenyl phosphonate In dichloromethane at 20℃; for 3h; Acetylation;	97%
With aluminum triflate at 20℃; for 0.00555556h;	96%

Tetrahydrofurfuryl alcohol (97-99-4) + Diethyl carbonate (105-58-8) → carbonate d'ethyle et de (2-tetrahydrofuryl) methyle (108106-20-3)

Conditions	Yield
aluminum oxide; cesium fluoride at 129.85℃; for 0.5h;	99%
With MgLa mixed oxide at 125℃; for 4h;	99%
tiveTMNano*MgO*Plus*(NAP-MgO,*Aerogel*prepared) at 125℃; for 3h;	99%
With immobilized 1,5,7-triazabicyclo[4.4.0]dec-5-ene on magnetic γ-Fe2O3 nanoparticles at 125℃; for 10h;	93%

Tetrahydrofurfuryl alcohol (97-99-4) + 1,1,3,3-tetramethyldisilazane (15933-59-2) → 1,1,3,3-tetramethyl-1,3-bis[(tetrahydrofuran-2-yl)methoxy]disiloxane (1333319-95-1)

Conditions	Yield
With 1.2% Pd/C at 20℃; for 20h; Inert atmosphere;	99%

Tetrahydrofurfuryl alcohol (97-99-4) + uranyl nirate hexahydrate → C13H26N2O10U

Conditions	Yield
In chloroform at 20℃; for 0.166667h;	99%

Tetrahydrofurfuryl alcohol (97-99-4) + 5-bromo-6-chloropyridine-2-carboxylic acid (959958-25-9) → 5-bromo-6-(tetrahydrofuran-2-ylmethoxy)pyridine-2-carboxylic acid (1415899-56-7)

Conditions	Yield
Stage #1: 5-bromo-6-chloropyridine-2-carboxylic acid With potassium hydroxide In dimethyl sulfoxide at 20℃; for 0.25h; Stage #2: Tetrahydrofurfuryl alcohol In dimethyl sulfoxide at 20℃; for 24h;	99%
Stage #1: 5-bromo-6-chloropyridine-2-carboxylic acid With potassium hydroxide In dimethyl sulfoxide at 20℃; for 0.25h; Stage #2: Tetrahydrofurfuryl alcohol In dimethyl sulfoxide at 20℃; for 24h; Stage #3: With hydrogenchloride In water	99%
Stage #1: 5-bromo-6-chloropyridine-2-carboxylic acid With potassium hydroxide In dimethyl sulfoxide at 20℃; for 0.25h; Stage #2: Tetrahydrofurfuryl alcohol In dimethyl sulfoxide at 20℃; for 24h;	99%

Tetrahydrofurfuryl alcohol (97-99-4) + (R)-2-[4-[(6-chloro-2-quinoxalinyl)oxy]phenoxy]propanoic acid ethyl ester (76578-14-8) → (RS)-tetrahydrofuran-2-ylmethyl (R)-2-[4-(6-chloro-2-quinoxalinyloxy)phenoxy]propionate (200509-41-7)

Conditions	Yield
Stage #1: Tetrahydrofurfuryl alcohol; (R)-2-[4-[(6-chloro-2-quinoxalinyl)oxy]phenoxy]propanoic acid ethyl ester In toluene at 115℃; for 2h; Stage #2: With tetraisopropanoyl titanate In toluene at 80 - 130℃; for 4h;	98.6%
With di(n-butyl)tin oxide at 75 - 130℃; for 8h; Temperature; Concentration;	98%

Tetrahydrofurfuryl alcohol (97-99-4) + methanesulfonyl chloride (124-63-0) → tetrahydro-2-furanmethanol methanesulfonate (ester) (72641-13-5)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 36h;	98%
With triethylamine In dichloromethane at 0℃; for 14h;	92%
With pyridine at 20℃; for 60h; Inert atmosphere; Cooling with ice;	77%

Tetrahydrofurfuryl alcohol (97-99-4) + lithium succinate (16090-09-8, 17229-80-0, 29126-50-9) → (tetrahydrofuran-2-ylmethoxy)butanedioic acid

Conditions	Yield
With lanthanum(III) chloride at 140℃; for 7.7h;	97%

Tetrahydrofurfuryl alcohol (97-99-4) + neodymium chloride tris(isopropanol) → neodymium chloride tris(tetrahydrofurfuryl alcohol)

Conditions	Yield
In benzene addn. of lanthanide-compd. to anhyd. benzene containing ligand, refluxing for 4 h under exclusion of moisture; removal of isopropanol by azeotropical distn., removal of benzene, filtn., washing with dry benzene, drying for 4 h under reduced pressure, elem. anal.;	97%

Tetrahydrofurfuryl alcohol (97-99-4) + titanium tetrachloride (7550-45-0) → hydrogenchloride (7647-01-0) + titanium(IV) trichloride(tetrahydrofuran-2-methanolate)

Conditions	Yield
In hexane N2-atmosphere; alcohol dropvise addn. with stirring (pptn.); washing (n-hexane), drying (vac.); elem. anal.;	A n/a B 97%

Tetrahydrofurfuryl alcohol (97-99-4) + uranyl nirate hexahydrate → [UO2(κ2-nitrate)2(tetrahydrofurfuryl alcohol)]*H2O

Conditions	Yield
In chloroform at 20℃; for 48h;	97%

Tetrahydrofurfuryl alcohol (97-99-4) + benzoyl chloride (98-88-4) → (tetrahydrofuran-2-yl)methyl benzoate (2217-32-5)

Conditions	Yield
With iron In 1,2-dichloro-ethane at 84℃; for 3h; Schlenk technique; Inert atmosphere; regioselective reaction;	97%

Tetrahydrofurfuryl alcohol (97-99-4) + carbon monoxide (201230-82-2) + tert-butyl alcohol (75-65-0) → (tetrahydrofuran-2-yl)methyl 3-methylbutanoate

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; α,α′-bis(2-pyridyl(tert-butyl)phosphino)-o-xylene; toluene-4-sulfonic acid at 120℃; under 15001.5 Torr; for 20h; Autoclave; Inert atmosphere;	97%

Tetrahydrofurfuryl alcohol (97-99-4) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → trimethyl(tetrahydro-2-furylmethoxy)silane (3067-36-5)

Conditions	Yield
With aluminum tris(dihydrogen phosphate) at 20℃; for 0.2h;	96%
With zinc(II) oxide at 20℃; for 1.83333h;	95%
With Al2O3*HClO4 In acetonitrile at 20℃; for 0.116667h;	93%

Tetrahydrofurfuryl alcohol (97-99-4) + 3-chloro-3-oxopropanoic acid methyl ester (37517-81-0) → methyl tetrahydrofurfuryl malonate (1198472-57-9)

Conditions	Yield
With pyridine In dichloromethane at 0℃; for 1.5h; Inert atmosphere;	96%

Tetrahydrofurfuryl alcohol (97-99-4) + m-methoxyphenylacetic acid (1798-09-0) → tetrahydrofurfuryl 3-methoxyphenylacetate (1198472-48-8)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; Inert atmosphere;	96%

Tetrahydrofurfuryl alcohol (97-99-4) + o-methylphenylacetic acid (644-36-0) → C14H18O3

Conditions	Yield
With β-cyclodextrin-SO3H In neat (no solvent) at 70℃; for 3h;	96%

Tetrahydrofurfuryl alcohol (97-99-4) + methacrylic acid methyl ester (80-62-6) → (tetrahydrofuran-2-yl)methyl 2-methylprop-2-enoate (2455-24-5)

Conditions	Yield
With 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy; di(n-butyl)tin oxide In 2-Methylpentane; cyclohexane at 85 - 100℃; for 12h; Temperature;	95%
2-methyl-propan-2-ol; lanthanum tri-tert-butylate at 25℃; for 2h;	32 %Chromat.
sodium ethanolate	15 %Chromat.
With sulfuric acid; benzene

Tetrahydrofurfuryl alcohol (97-99-4) + Carbonic acid benzyl ester 6-trifluoromethyl-benzotriazol-1-yl ester (112380-58-2) → Carbonic acid benzyl ester furan-2-ylmethyl ester (112380-52-6)

Conditions	Yield
With dmap In tetrahydrofuran at 0℃; for 24h;	95%

Tetrahydrofurfuryl alcohol (97-99-4) + sodium succinate (150-90-3) → malic acid (617-48-1) + (tetrahydrofuran-2-ylmethoxy)butanedioic acid

Conditions	Yield
With lanthanum(III) chloride at 116℃; for 19h; Product distribution; also with other alcohols; variation of reaction time, temperature and proportion of reagents;	A 3% B 95%

Upstream product

• 98-00-0 Furfuryl alcohol 
• 98-01-1 Furfural 
• 1333-74-0 Hydrogen 

Downstream Products

• 82500-35-4 1-TETRAHYDROFURFURYL-PIPERAZINE 
• 14484-47-0 Deflazacort 
• 3003-84-7 Tetrahydrofurfuryl chloride 
• 110-87-2 3,4-Dihydro-2H-pyran 
• 26116-12-1 2-(Aminomethyl)-1-ethylpyrrolidine 
• 1192-30-9 Tetrahydrofurfuryl bromide 
• 111-29-5 1,5-Pentanediol 
• 87392-05-0 (R)-(+)-2-Tetrahydrofuroic acid 
• 637-64-9 TETRAHYDROFURFURYL ACETATE 

Recommend Products

• 497-06-3  3,4-butenediol 
• 60-29-7  diethyl ether 
• 821-11-4  trans-butene-1,4-diol 
• 120343-27-3  5-chloropentane-1,4-diol 
• 5470-02-0  N-propylpiperidine 
• 7179-87-5  N-propyltetrahydrofurfurylamine 
• 107-12-0  propiononitrile 
• 766-09-6  1-ethyl-piperidine 
• 7179-86-4  N-((tetrahydrofuran-2-yl)methyl)ethanamine 
• 75-05-8  acetonitrile 
• 4945-48-6  1-butyl-piperidine 
• 55100-03-3  N-butyltetrahydrofurfurylamine 
• 109-74-0  propyl cyanide 
• 109-99-9  tetrahydrofuran