Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane for 3h; Reflux; | 97% |
With 1,4-diaza-bicyclo[2.2.2]octane; carbonic acid dimethyl ester at 90℃; for 2h; Reagent/catalyst; Time; | 92% |
With phosphorus pentoxide | |
Multi-step reaction with 2 steps 1: pyridine; PBr3 2: aqueous alkaline solution View Scheme |
Conditions | Yield |
---|---|
With sodium hydroxide; (C16H33CH3)2NCH2CH2N(CH3)2C16H33)(2+)*Br(1-)*Br(1-) In water Heating; | 89% |
With sodium hydroxide; (C16H33N(CH3)2CH2CH=CHCH2(CH3)2NC16H33)(2+)*Br(1-)*Br(1-) In water Heating; | 84% |
With potassium carbonate In ethylene glycol; ethyl acetate Reflux; | 81% |
2-(2-bromophenoxy)ethan-1-ol
benzo-1,4-dioxane
Conditions | Yield |
---|---|
With palladium diacetate; 9-di(2-tert-butylphosphinophenyl)phenanthrene; caesium carbonate In toluene at 70℃; for 40h; | 88% |
With palladium diacetate; caesium carbonate; 2'-(di-tert-butylphosphanyl)-N,N-dimethyl-[1,1'-biphenyl]-2-amine In toluene at 70℃; for 40h; | 88% |
With (4,4′-di-tert-butyl-2,2′-dipyridyl)Ni(o-tolyl)(Br); 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 80℃; for 24h; Inert atmosphere; Sealed tube; UV-irradiation; | 86% |
[1,3]-dioxolan-2-one
benzene-1,2-diol
A
benzo-1,4-dioxane
B
2,2'-(1,2-phenylenedioxy)diethanol
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In N,N-dimethyl-formamide at 170℃; for 1h; Inert atmosphere; Schlenk technique; | A 5% B 84% |
6-bromo-1,4-benzodioxane
benzo-1,4-dioxane
Conditions | Yield |
---|---|
With tetrabutylammonium tetrafluoroborate; triethylamine In tetrahydrofuran; acetonitrile at 20℃; for 4.4h; Inert atmosphere; Electrolysis; | 83% |
With isopropyl alcohol for 20h; Schlenk technique; Inert atmosphere; Irradiation; Heating; | 65% |
Conditions | Yield |
---|---|
Stage #1: benzene-1,2-diol With caesium carbonate In dichloromethane at 20℃; for 0.166667h; Inert atmosphere; Stage #2: (vinylselenonyl)benzene In dichloromethane at 0 - 20℃; for 24h; Reagent/catalyst; Temperature; Time; Inert atmosphere; | 80% |
Conditions | Yield |
---|---|
With chlorobis(cyclooctene)-iridium(I) dimer; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; lithium chloride In water; 1,3,5-trimethyl-benzene at 170℃; for 60h; Schlenk technique; Inert atmosphere; | 79% |
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; lithium chloride In water; 1,3,5-trimethyl-benzene for 60h; Reflux; | 79% |
Conditions | Yield |
---|---|
With caesium carbonate; triphenylphosphine; palladium dichloride In toluene at 50℃; for 24h; | 65% |
Conditions | Yield |
---|---|
With caesium carbonate; triphenylphosphine; palladium dichloride In toluene at 50℃; for 24h; | 63% |
Conditions | Yield |
---|---|
With sodium hydroxide In dimethyl sulfoxide | 57% |
With sodium hydroxide In N,N-dimethyl-formamide at 90℃; | 2.1 g |
With sodium hydroxide In dimethyl sulfoxide at 80 - 85℃; for 5.45h; | 115 g |
2-fluorophenol
2-chloro-ethanol
A
benzo-1,4-dioxane
B
2-hydroxyphenyl 2-chloroethyl ether
Conditions | Yield |
---|---|
With <(η-C6H6)Rh(η-C5EtMe4)>(2+)*2 In nitromethane at 80℃; for 48h; Title compound not separated from byproducts; | A 50% B 10 % Chromat. |
2-Phenoxyethanol
A
benzo-1,4-dioxane
B
6-iodo-1,4-benzodioxane
C
2-(4-iodophenoxy)ethanol
Conditions | Yield |
---|---|
With [bis(acetoxy)iodo]benzene; iodine In 1,2-dichloro-ethane at 60 - 70℃; Irradiation; | A 39% B 12% C n/a |
With [bis(acetoxy)iodo]benzene; iodine In 1,2-dichloro-ethane at 60 - 70℃; Irradiation; | A 6% B 22% C n/a |
Conditions | Yield |
---|---|
With [bis(acetoxy)iodo]benzene; iodine In 1,2-dichloro-ethane at 60 - 70℃; for 2h; Irradiation; | A 39% B 12% |
With [bis(acetoxy)iodo]benzene; iodine In 1,2-dichloro-ethane at 60 - 70℃; for 2h; Irradiation; | A 6% B 22% |
Conditions | Yield |
---|---|
(η5-ethyltetramethylcyclopentadienyl)(η6-benzene)rhodium(III) tetrafluoroborate In nitromethane; acetone at 80℃; for 312h; | 35% |
2-(2-bromo-ethoxy)-phenol
benzo-1,4-dioxane
Conditions | Yield |
---|---|
With alkaline solution | |
With potassium hydroxide In water; dimethyl sulfoxide at 25℃; | 92 % Spectr. |
With potassium hydroxide In water; dimethyl sulfoxide at 25℃; Rate constant; | 92 % Spectr. |
1-(benzyloxy)-2-(2-bromoethoxy)benzene
benzo-1,4-dioxane
Conditions | Yield |
---|---|
With hydrogenchloride; ethanol |
oxirane
phenylium
A
1-benzofurane
B
2,3-Dihydrobenzofuran
C
benzo-1,4-dioxane
D
vinyl phenyl ether
Conditions | Yield |
---|---|
With oxygen; trimethylamine under 244 Torr; for 8760h; Ambient temperature; dark; | A 4 % Chromat. B 15 % Chromat. C 3 % Chromat. D 78 % Chromat. |
With oxygen; trimethylamine under 244 Torr; for 8760h; Product distribution; Mechanism; Ambient temperature; arylation of various cyclic ethers in the dark and effects of base; | A 4 % Chromat. B 15 % Chromat. C 3 % Chromat. D 78 % Chromat. |
oxirane
phenylium
A
1-benzofurane
B
2,3-Dihydrobenzofuran
C
benzo-1,4-dioxane
D
phenol
Conditions | Yield |
---|---|
With oxygen under 34 Torr; for 8760h; Ambient temperature; dark; | A 2 % Chromat. B 21 % Chromat. C 61 % Chromat. D 15 % Chromat. |
oxirane
phenylium
A
1-benzofurane
B
2,3-Dihydrobenzofuran
C
benzo-1,4-dioxane
D
vinyl phenyl ether
E
phenol
Conditions | Yield |
---|---|
With oxygen under 34 Torr; for 8760h; Product distribution; Mechanism; Ambient temperature; arylation of various cyclic ethers in the dark; | A 2 % Chromat. B 21 % Chromat. C 61 % Chromat. D 1 % Chromat. E 15 % Chromat. |
oxirane
phenylium
A
2,3-Dihydrobenzofuran
B
benzo-1,4-dioxane
C
phenol
Conditions | Yield |
---|---|
With oxygen under 224 Torr; for 8760h; Ambient temperature; dark; | A 37 % Chromat. B 33 % Chromat. C 30 % Chromat. |
Conditions | Yield |
---|---|
With bis(benzonitrile)palladium(II) dichloride In benzene Heating; | 50 % Chromat. |
Conditions | Yield |
---|---|
With <(η-C6H6)Rh(η-C5EtMe4)>(2+)*2; triethylamine 1) CH3NO2, 80 deg C, 2 d, 2) room temperature, 24 h; Yield given. Multistep reaction. Title compound not separated from byproducts; |
1,10-Dimethyl-2,9,11,12,13-pentaoxa-tricyclo[8.2.1.03,8]trideca-3,5,7-triene
benzo-1,4-dioxane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: CH2Cl2 / 1 h / -78 °C / Irradiation 2: potassium carbonate / ethane-1,2-diol / 4 h / 120 °C View Scheme |
2,9,11,12,13-Pentaoxa-tricyclo[8.2.1.03,8]trideca-3,5,7-triene
benzo-1,4-dioxane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 51 percent / CH2Cl2 / 1 h / -78 °C / Irradiation 2: potassium carbonate / ethane-1,2-diol / 4 h / 120 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aqueous NaOH 2: phosphorus (V)-oxide View Scheme | |
Multi-step reaction with 3 steps 1: sodium ethylate; ethanol 2: pyridine; PBr3 3: aqueous alkaline solution View Scheme |
2,3-dibromo-2,3-dihydro-benzo[1,4]dioxin
benzo-1,4-dioxane
Conditions | Yield |
---|---|
With sodium iodide In acetone for 2h; Heating / reflux; |
2-(2-hydroxy-phenoxy)-ethanol
carbonic acid dimethyl ester
A
benzo-1,4-dioxane
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane at 90℃; for 24h; | A 10 %Chromat. B 90 %Chromat. |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 150 °C / Autoclave 2: 1,4-diaza-bicyclo[2.2.2]octane / 3 h / Reflux View Scheme |
benzo-1,4-dioxane
6-bromo-1,4-benzodioxane
Conditions | Yield |
---|---|
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; | 100% |
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 24h; | 100% |
With N-Bromosuccinimide In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 24h; | 100% |
Conditions | Yield |
---|---|
With sulfuric acid; sodium perchlorate In chloroform Heating; or KClO4; | 100% |
benzo-1,4-dioxane
tert-butyl alcohol
6-tert-Butyl-2,3-dihydro-benzo[1,4]dioxine
Conditions | Yield |
---|---|
With sulfuric acid; sodium perchlorate In chloroform Heating; or KClO4; | 100% |
benzo-1,4-dioxane
2-bromo-5-iodobenzoyl chloride
(2-bromo-5-iodophenyl)-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methanone
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at 20℃; for 3h; Temperature; | 100% |
With aluminum (III) chloride In dichloromethane at -5 - 20℃; for 4h; Inert atmosphere; | 90% |
In dichloromethane at 0 - 20℃; |
2-chloro-5-iodobenzoylchloride
benzo-1,4-dioxane
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at 20℃; for 16h; | 98.7% |
benzo-1,4-dioxane
2,3-dihydro-benzo[1,4]dioxin-6-sulfonic acid
Conditions | Yield |
---|---|
With sulfur trioxide In 1,4-dioxane-d8 at 15℃; for 0.25h; other time; other temp; other reagent: cc H2SO4; | 98% |
With sulfuric acid at 125℃; |
benzo-1,4-dioxane
Conditions | Yield |
---|---|
With sulfur trioxide In nitromethane at 10℃; for 0.25h; other reagent; | 98% |
benzo-1,4-dioxane
5-bromo-2-methylbenzoyl chloride
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at 20℃; Inert atmosphere; | 96% |
With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 12h; | 95% |
benzo-1,4-dioxane
phenyl isothiocyanate
2-(2,3-dihydrobenzo[b][1,4]dioxin-2-yl)benzo[d]thiazole
Conditions | Yield |
---|---|
With di-tert-butyl peroxide; copper diacetate In acetonitrile at 120℃; for 6h; Inert atmosphere; | 94% |
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at -10 - 20℃; for 1.5h; | 93.1% |
benzo-1,4-dioxane
benzoyl chloride
2,3-dihydro-1,4-benzodioxin-6-yl(phenyl)methanone
Conditions | Yield |
---|---|
With aluminium trichloride In nitrobenzene at 5℃; for 6h; | 92.9% |
With aluminium trichloride In 1,2-dichloro-ethane at 20℃; for 10h; | 88% |
With aluminium trichloride In dichloromethane at 0℃; for 1h; | 85% |
With aluminium trichloride In dichloromethane at 15℃; for 1h; | |
With aluminium trichloride In benzene at 55 - 60℃; for 2.5h; Friedel-Crafts reaction; |
Conditions | Yield |
---|---|
92% | |
With aluminium trichloride In carbon disulfide for 10h; Ambient temperature; | 91% |
With aluminium trichloride In benzene at 55 - 60℃; for 2.5h; Friedel-Crafts reaction; |
benzo-1,4-dioxane
tertiary butyl chloride
6-tert-Butyl-2,3-dihydro-benzo[1,4]dioxine
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at -10 - 20℃; for 1.5h; | 91.2% |
benzo-1,4-dioxane
6,7-dibromo-2,3-dihydrobenzo[b][1,4]dioxine
Conditions | Yield |
---|---|
With bromine In dichloromethane at 20℃; | 90% |
With bromine In dichloromethane at 20℃; Inert atmosphere; | 83% |
With iodine pentoxide; potassium bromide In water at 20℃; for 23h; regioselective reaction; | 78% |
benzo-1,4-dioxane
4-fluorobenzoyl chloride
(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-(4-fluoro-phenyl)-methanone
Conditions | Yield |
---|---|
With aluminium trichloride In dichloromethane at 15℃; for 1h; | 90% |
benzo-1,4-dioxane
4-chlorobenzoyl chloride
(4-Bromo-phenyl)-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-methanone
Conditions | Yield |
---|---|
With aluminium trichloride In dichloromethane at 15℃; for 1h; | 90% |
Conditions | Yield |
---|---|
With C19H16*C24BF20; C23H40NScSi2 In chlorobenzene at 70℃; for 2h; stereoselective reaction; | 90% |
benzo-1,4-dioxane
3,4,5-Trimethoxybenzoyl chloride
6-(3,4,5-trimethoxybenzoyl)-2,3-dihydro-1,4-benzodioxin
Conditions | Yield |
---|---|
With tin(IV) chloride In dichloromethane for 24h; Ambient temperature; | 88% |
benzo-1,4-dioxane
Conditions | Yield |
---|---|
With disulfur dichloride; acetic acid at 20℃; for 120h; Inert atmosphere; Schlenk technique; Glovebox; | 88% |
With disulfur dichloride In acetic acid for 18h; | 52% |
Stage #1: benzo-1,4-dioxane With disulfur dichloride In acetic acid at 20℃; for 48h; Stage #2: With tin(ll) chloride In methanol; acetic acid | |
With disulfur dichloride; acetic acid at 20℃; Inert atmosphere; Schlenk technique; | 2.45 g |
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at -10 - 20℃; for 1.5h; | 87.5% |
benzo-1,4-dioxane
6-nitro-2,3-dihydrobenzo[b][1,4]dioxine
Conditions | Yield |
---|---|
With nitric acid at 60℃; | 87% |
With tert.-butylnitrite In acetonitrile at 20℃; for 1h; | 80% |
With nitric acid In water at 20 - 80℃; for 6h; | 76.7% |
Conditions | Yield |
---|---|
With (C5H5)Y(CH2C6H4NMe2-o)2; trityl tetrakis(pentafluorophenyl)borate In toluene at 70℃; for 24h; Inert atmosphere; Glovebox; regioselective reaction; | 87% |
Conditions | Yield |
---|---|
Stage #1: benzo-1,4-dioxane; formaldehyd With acetic acid at 0℃; for 0.5h; Inert atmosphere; Stage #2: With hydrogen bromide; acetic acid at 0 - 20℃; Inert atmosphere; | 87% |
benzo-1,4-dioxane
6-iodo-1,4-benzodioxane
Conditions | Yield |
---|---|
With Iron(III) nitrate nonahydrate; carbon dioxide; iodine; oxygen In ethylene glycol at 100℃; under 5250.53 - 9000.9 Torr; for 10h; Autoclave; Green chemistry; regioselective reaction; | 86% |
With iodine; periodic acid In ethanol for 0.75h; Heating; | 73% |
Conditions | Yield |
---|---|
With manganese(III) triacetate dihydrate In acetic acid at 60℃; for 5h; | 85% |
Conditions | Yield |
---|---|
With Amberlyst-15 In neat (no solvent) at 60℃; for 0.666667h; Friedel-Crafts Alkylation; Green chemistry; | 85% |
benzo-1,4-dioxane
hydrocinnamic acid chloride
1-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-phenylpropan-1-one
Conditions | Yield |
---|---|
With aluminium trichloride In dichloromethane at 30℃; for 1h; | 84% |
With aluminium trichloride In dichloromethane at 15 - 20℃; for 3h; | 78% |
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