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Conditions | Yield |
---|---|
With 1-Iodooctane at 146℃; | A n/a B n/a C n/a D 100% |
Conditions | Yield |
---|---|
With 1-bromo-octane at 146℃; | A n/a B n/a C n/a D 100% |
Conditions | Yield |
---|---|
With potassium hydroxide; aliquat 366 In neat (no solvent) at 20℃; for 2h; | 98% |
With potassium hydroxide; tetrabutylammomium bromide; potassium carbonate at 158℃; for 0.0152778h; | 90% |
With sodium In xylene |
Conditions | Yield |
---|---|
With Dimethylphenylsilane In 1,1,2,2-tetrachloroethane at 100℃; for 3h; | 98% |
With hydrogen; Pd-C | 93% |
With triethylsilane; bismuth(III) bromide In acetonitrile for 2h; Ambient temperature; | 88% |
With Dimethylphenylsilane In 1,1,2,2-tetrachloroethane at 100℃; for 3h; chemoselective reaction; |
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal at 160℃; under 760 Torr; for 18h; Etherification; | 97% |
With hydrogen; palladium on activated charcoal at 160℃; for 10h; atmospheric pressure; | 97% |
With Pd/Al2O3; hydrogen; ethyl iodide at 60℃; under 15001.5 Torr; for 15h; Sealed tube; |
Conditions | Yield |
---|---|
With yttrium iron garnet In neat (no solvent) at 80℃; for 0.25h; Green chemistry; | 93% |
With C19H26IrN3O2(2+)*2C2F6NO4S2(1-); hydrogen In toluene at 160℃; for 20h; Reagent/catalyst; Temperature; | 90% |
With boron tri(hydrogen sulphate); silica gel at 60℃; for 0.116667h; Neat (no solvent); | 87% |
trimethyl phosphite
octanol
A
1-methoxyoctane
B
di-n-octyl ether
Conditions | Yield |
---|---|
With bismuth(lll) trifluoromethanesulfonate In neat (no solvent) at 100℃; Reagent/catalyst; | A 91% B 6% |
octanol
benzyl alcohol
A
di-n-octyl ether
B
dibenzyl ether
C
((octyloxy)methyl)benzene
Conditions | Yield |
---|---|
With copper acetylacetonate; carbon tetrabromide at 150℃; for 8h; Inert atmosphere; Sealed tube; | A 10% B 18% C 82% |
trimethyl(oct-1-yloxy)silane
di-n-octyl ether
Conditions | Yield |
---|---|
With sulfuric acid; silica gel In hexane at 20℃; for 0.25h; | 80% |
With Nafion-H(R) In hexane at 20℃; for 0.333333h; | 80% |
carbon-based solid acid In hexane at 20℃; for 0.133333h; | 80% |
1-Chlorooctane
A
octanol
B
1-Fluoro-octane
C
oct-1-ene
D
di-n-octyl ether
E
octyl formate
Conditions | Yield |
---|---|
With potassium fluoride; formamide; tetrabutylammomium bromide at 120℃; for 72h; Mechanism; Product distribution; vari. of proportion of reagents, time, also with chlorure de benzyl and chlorure de phenethyl; | A 8% B 72% C 4% D 4% E 4% |
With potassium fluoride In formamide at 120℃; for 3h; Product distribution; effect of change water to formamide as solvent, reaction time, effect of molar ratio of KF/HCONH2; | A 8.0 % Chromat. B 72.3 % Chromat. C 4.5 % Chromat. D 4.3 % Chromat. E 3.7 % Chromat. |
1-Chlorooctane
A
octanol
B
1-Fluoro-octane
C
di-n-octyl ether
D
octyl formate
Conditions | Yield |
---|---|
With potassium fluoride; formamide; tetrabutylammomium bromide at 120℃; for 72h; Further byproducts given; | A 72% B 72% C 4% D 4% |
With potassium fluoride; formamide; tetrabutylammomium bromide at 120℃; for 72h; Further byproducts given; | A 8% B 72% C 4% D 4% |
With potassium fluoride; formamide; tetrabutylammomium bromide at 120℃; for 72h; Further byproducts given; | A 8% B 72% C 72% D 4% |
With potassium fluoride; formamide; tetrabutylammomium bromide at 120℃; for 72h; Further byproducts given; | A 8% B 72% C 4% D 72% |
4-tetrahydrofuran-2-yl-butan-2-ol
A
octanol
B
di-n-octyl ether
Conditions | Yield |
---|---|
With hydrogen; 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide at 150℃; under 90009 Torr; for 4h; Autoclave; | A 29% B 66% |
With 2.5% Ru/[BSO3BIM][NTf2]; hydrogen at 150℃; under 90009 Torr; for 15h; Reagent/catalyst; | A 44.9% B 26.1% |
With 5% active carbon-supported ruthenium; hydrogen at 150℃; under 60006 Torr; for 6h; Reagent/catalyst; Autoclave; |
4-tetrahydrofuran-2-yl-butan-2-ol
A
octanol
B
ethyl octyl ether
C
di-n-octyl ether
Conditions | Yield |
---|---|
With hydrogen; 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide at 150℃; under 90009 Torr; for 4h; Autoclave; | A 25% B 7% C 66% |
n-octyl triflate
B
di-n-octyl ether
C
CHF3O3S*C12H23N
D
octyl 2-cyanoacetate
E
2-cyanoacrylic acid
Conditions | Yield |
---|---|
With trifluoroacetic acid In dichloromethane at 22℃; Product distribution / selectivity; | A 65% B n/a C n/a D n/a E n/a |
octanol
A
trans-4-Octene
B
(E)-3-octene
C
trans-2-Octene
D
oct-1-ene
E
di-n-octyl ether
Conditions | Yield |
---|---|
Act Alu at 270℃; Product distribution; various temperatures, also using Act Alu Cl and Alu C Cl as catalysts; | A n/a B n/a C n/a D n/a E 60% |
4-tetrahydrofuran-2-yl-butan-2-ol
A
2-propyltetrahydropyran
B
octanol
C
di-n-octyl ether
Conditions | Yield |
---|---|
With hydrogen; 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide at 150℃; under 90009 Torr; for 4h; Autoclave; | A 6% B 28% C 60% |
4-tetrahydrofuran-2-yl-butan-2-ol
A
2-butanyltetrahydrofuran
B
octanol
C
di-n-octyl ether
Conditions | Yield |
---|---|
With ruthenium-carbon composite; 1-(4-butylcarboxylic acid)-3-(n-butyl)-imidazolium bis(trifluoromethylsulfonyl)imide; hydrogen at 150℃; under 90009 Torr; for 15h; Reagent/catalyst; Ionic liquid; | A 58.6% B 27.1% C 9.1% |
With 1-(4-butylcarboxylic acid)-3-(n-butyl)-imidazolium bis(trifluoromethylsulfonyl)imide; hydrogen at 150℃; under 90009 Torr; for 15h; Reagent/catalyst; Ionic liquid; | A 25.8% B 44.9% C 26.1% |
With N,N,N-tributyl-1-(4-butylsulfonic acid)-aminium bis(trifluoromethylsulfonyl)imide; hydrogen at 150℃; under 90009 Torr; for 15h; Reagent/catalyst; Ionic liquid; | A 11.7% B 41.5% C 34.5% |
With 5 wt% ruthenium/carbon; hydrogen at 150℃; under 90009 Torr; for 15h; Ionic liquid; |
1-bromo-octane
potassium octylate
A
oct-1-ene
B
di-n-octyl ether
Conditions | Yield |
---|---|
With Aliquat 336 at 100℃; for 7h; | A 35% B 57% |
4-(furan-2-yl)but-3-en-2-one
A
octane
B
octanol
C
di-n-octyl ether
Conditions | Yield |
---|---|
Stage #1: 4-(furan-2-yl)but-3-en-2-one With ruthenium-carbon composite; hydrogen; toluene-4-sulfonic acid at 120℃; under 90009 Torr; for 2h; Stage #2: With hydrogen at 150℃; under 90009 Torr; for 45h; Reagent/catalyst; Acidic conditions; Ionic liquid; | A 16.9% B 18.1% C 53% |
Stage #1: 4-(furan-2-yl)but-3-en-2-one With ruthenium-carbon composite; hydrogen at 120℃; under 90009 Torr; for 2h; Stage #2: With toluene-4-sulfonic acid at 150℃; under 90009 Torr; for 45h; Ionic liquid; | A 16.9% B 18.1% C 53% |
4-tetrahydrofuran-2-yl-butan-2-ol
A
2-butanyltetrahydrofuran
B
octane
C
octanol
D
di-n-octyl ether
Conditions | Yield |
---|---|
With ruthenium-carbon composite; hydrogen; toluene-4-sulfonic acid at 150℃; under 90009 Torr; for 15h; Reagent/catalyst; | A 8.7% B 8.5% C 24.7% D 51.9% |
4-tetrahydrofuran-2-yl-butan-2-ol
A
octane
B
octanol
C
di-n-octyl ether
Conditions | Yield |
---|---|
With 5% active carbon-supported ruthenium; hydrogen; toluene-4-sulfonic acid at 150℃; under 90009 Torr; for 15h; | A 8.5% B 24.7% C 51.9% |
4-(furan-2-yl)but-3-en-2-one
A
2-methyl-5-propyl-tetrahydrofuran
B
octane
C
di-n-octyl ether
Conditions | Yield |
---|---|
With palladium/alumina; niobium phosphate; hydrogen In cyclohexane at 170℃; under 15001.5 Torr; for 24h; Inert atmosphere; | A 16% B 51% C 20% |
4-(furan-2-yl)but-3-en-2-one
A
2-butanyltetrahydrofuran
B
octanol
C
di-n-octyl ether
Conditions | Yield |
---|---|
Stage #1: 4-(furan-2-yl)but-3-en-2-one With ruthenium-carbon composite; 1-(4-butylcarboxylic acid)-3-(n-butyl)-imidazolium bis(trifluoromethylsulfonyl)imide; hydrogen at 120℃; under 90009 Torr; for 2h; Ionic liquid; Stage #2: With hydrogen at 150℃; under 90009 Torr; for 45h; Reagent/catalyst; Acidic conditions; Ionic liquid; | A 5.4% B 48.4% C 44.2% |
Stage #1: 4-(furan-2-yl)but-3-en-2-one With 5 wt% ruthenium/carbon; hydrogen at 120℃; under 90009 Torr; for 2h; Stage #2: With hydrogen at 150℃; under 90009 Torr; for 60h; Ionic liquid; |
Conditions | Yield |
---|---|
Stage #1: 4-(furan-2-yl)but-3-en-2-one With ruthenium-carbon composite; hydrogen at 120℃; under 90009 Torr; for 2h; Stage #2: With 4-(3'-butyl-1'-imidazolio)-1-butanesulfonic acid bis(trifluoromethylsulfonyl)imidide at 150℃; under 90009 Torr; for 45h; Time; Ionic liquid; | A 48.4% B 44.2% |
Stage #1: 4-(furan-2-yl)but-3-en-2-one With 5 wt% ruthenium/carbon; hydrogen at 120℃; under 90009 Torr; for 2h; Stage #2: With hydrogen at 150℃; under 90009 Torr; for 60h; Ionic liquid; | |
Multi-step reaction with 2 steps 1: hydrogen; 5% active carbon-supported ruthenium / cyclohexane / 2 h / 50 °C / 60006 Torr / Autoclave 2: hydrogen; 5% active carbon-supported ruthenium / 6 h / 150 °C / 60006 Torr / Autoclave View Scheme |
1-bromo-octane
potassium hydrogencarbonate
A
di-n-octyl ether
B
dioctyl carbonate
Conditions | Yield |
---|---|
tetrabutyl phosphonium bromide In various solvent(s) at 150℃; Solvent: NMP; | A n/a B 47% |
Conditions | Yield |
---|---|
With sodium hydroxide; triphenylmethyl alcohol; tetrabutylammomium bromide In 1,2-dichloro-benzene at 105℃; for 1.5h; phase transfer conditions; | A 45% B n/a |
4-(furan-2-yl)but-3-en-2-one
A
2-methyl-5-propyl-tetrahydrofuran
B
2-butanyltetrahydrofuran
C
octane
D
di-n-octyl ether
Conditions | Yield |
---|---|
With hydrogen In cyclohexane at 170℃; under 15001.5 Torr; for 24h; Reagent/catalyst; Inert atmosphere; | A 37% B 17% C 24% D 5% |
With hydrogen In cyclohexane at 170℃; under 18751.9 Torr; for 24h; Autoclave; Sealed tube; |
furfural
acetone
A
2-butanyltetrahydrofuran
B
octanol
C
di-n-octyl ether
Conditions | Yield |
---|---|
Stage #1: furfural; acetone With sodium hydroxide at 20℃; for 15h; Stage #2: With ruthenium-carbon composite; 1-(4-butylcarboxylic acid)-3-(n-butyl)-imidazolium bis(trifluoromethylsulfonyl)imide; hydrogen at 120℃; under 90009 Torr; for 2h; Ionic liquid; Stage #3: With hydrogen at 150℃; under 90009 Torr; for 60h; Acidic conditions; Ionic liquid; | A 23.5% B 32.5% C 19.8% |
Stage #1: furfural; acetone With sodium hydroxide at 20℃; for 16h; Stage #2: With ruthenium-carbon composite; hydrogen at 120℃; under 90009 Torr; for 2h; Ionic liquid; Stage #3: With ruthenium-carbon composite; hydrogen at 150℃; under 90009 Torr; for 60h; Ionic liquid; |
Conditions | Yield |
---|---|
With hafnium(IV) trifluoromethanesulfonate; palladium 10% on activated carbon; hydrogen In neat (no solvent) at 125℃; under 750.075 Torr; for 18h; | 9% |
Multi-step reaction with 2 steps 1: hafnium tetrakis(trifluoromethanesulfonate); water / neat (no solvent) / 3 h / 170 °C 2: iron(III) trifluoromethanesulfonate / neat (no solvent) / 6 h / 180 °C View Scheme |
Conditions | Yield |
---|---|
With molybdenum(V) chloride In dichloromethane at 80℃; for 3h; | 93% |
With molybdenum(V) chloride In 1,2-dichloro-ethane at 80℃; for 3h; | 93 % Chromat. |
Conditions | Yield |
---|---|
With hafnium tetrakis(trifluoromethanesulfonate); palladium 10% on activated carbon; hydrogen In water at 180℃; under 30003 Torr; for 6h; Sealed tube; Inert atmosphere; Green chemistry; | 86% |
With di-tert-butyl peroxide; trichlorosilane at 140℃; for 16h; | 52 % Chromat. |
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrogen; hafnium tetrakis(trifluoromethanesulfonate) / water / 3 h / 180 °C / 30003 Torr / Sealed tube; Inert atmosphere; Green chemistry 2: palladium 10% on activated carbon; hydrogen; hafnium tetrakis(trifluoromethanesulfonate) / neat (no solvent) / 6 h / 180 °C / 30003 Torr / Sealed tube; Inert atmosphere; Green chemistry View Scheme |
Conditions | Yield |
---|---|
With sodium bromate; sodium hydrogensulfite In water at 20℃; for 16h; Oxidation; bromination; | A 18% B 82% C n/a |
With sodium bromate; sodium hydrogensulfite In water; acetonitrile at 20℃; for 16h; Oxidation; bromination; | A 27% B 67% C 1% |
With sodium bromate; sodium hydrogensulfite In water at 60℃; for 16h; Oxidation; bromination; | A 14% B 40% C 32% |
Conditions | Yield |
---|---|
With molybdenum(V) chloride In dichloromethane at 80℃; for 3h; | 82% |
di-n-octyl ether
Hexanoyl chloride
A
1-Chlorooctane
B
n-octyl hexanoate
Conditions | Yield |
---|---|
With molybdenum(V) chloride In 1,2-dichloro-ethane at 80℃; for 3h; | A 56% B 82% |
Conditions | Yield |
---|---|
Stage #1: propene With sulfur dioxide; boron trichloride In dichloromethane at -196 - -20℃; for 3h; Stage #2: di-n-octyl ether In dichloromethane for 48h; | 79% |
Conditions | Yield |
---|---|
With molybdenum(V) chloride In dichloromethane at 80℃; for 1h; | 78% |
With rhenium(I) pentacarbonyl bromide In 1,2-dichloro-ethane at 80℃; for 5h; Inert atmosphere; | 35% |
di-n-octyl ether
benzoyl chloride
A
1-Chlorooctane
B
n-octyl benzoate
Conditions | Yield |
---|---|
With molybdenum(V) chloride In 1,2-dichloro-ethane at 80℃; for 1h; | A 34% B 78% |
Conditions | Yield |
---|---|
With dihydrogen peroxide; bromine In dichloromethane; water at 20℃; for 4h; | A 9% B 8% C 71% |
Conditions | Yield |
---|---|
With nitric acid In water at 50℃; for 2h; | 64% |
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid at 15℃; for 0.5h; Product distribution; Further Variations:; Reagents; | A 55% B n/a |
Conditions | Yield |
---|---|
With copper(II) acetate monohydrate; Selectfluor In diethyl ether; acetonitrile at 20℃; for 4h; | 54% |
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