Conditions | Yield |
---|---|
Stage #1: 3,4,5-trimethoxy-benzaldehyde With hydrazine hydrate; potassium hydroxide In ethylene glycol at 70℃; for 2h; Wolff-Kishner Reduction; Stage #2: In ethylene glycol at 150℃; for 2h; | 100% |
With hydrogenchloride; hydrogen; palladium on activated charcoal In methanol at 20℃; under 760.051 Torr; for 1.5h; | 98% |
With hydrogen; palladium on activated charcoal In acetic acid under 30002.4 Torr; for 72h; Ambient temperature; | 97% |
(2,3,4-trimethoxy-6-methylphenyl)boronic acid
N,N-diethyl-6-iodo-3-isopropoxy-2-(trimethylsilyl)benzamide
3,4,5-trimethoxytoluene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water Suzuki-Miyaura Coupling; Inert atmosphere; Reflux; | 100% |
(2,3,4-trimethoxy-6-methylphenyl)boronic acid
N,N-diethyl-2-iodo-5-isopropoxybenzamide
3,4,5-trimethoxytoluene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water Suzuki-Miyaura Coupling; Inert atmosphere; Reflux; | 100% |
1-(2-hexyl)-2,5-dimethylbenzene
toluene-4-sulfonic acid
3,4,5-trimethoxytoluene
Conditions | Yield |
---|---|
In water | 98.5% |
Conditions | Yield |
---|---|
98% |
3,4,5-trimethoxy-benzaldehyde
N-butylamine
A
N-butyl-3,4,5-trimethoxybenzylamine hydrochloride
B
3,4,5-trimethoxytoluene
Conditions | Yield |
---|---|
With chloroform; 10% Pd/C; hydrogen In methanol at 20℃; under 760.051 Torr; for 2h; chemoselective reaction; | A 97% B 4% |
methanol
3,4,5-trimethoxy-benzaldehyde
A
3,4,5-trimethoxytoluene
B
(3,4,5-trimethoxyphenyl)methanol
C
1,2,3-trimethoxy-5-(methoxymethyl)benzene
Conditions | Yield |
---|---|
With hydrogen; acetic acid; palladium on activated charcoal In methanol at 20℃; under 760.051 Torr; for 2h; | A 7% B 75% C 13% |
With hydrogen at 160℃; under 15001.5 Torr; for 4h; Autoclave; Green chemistry; | A 34.9 %Chromat. B 53 %Chromat. C 12.1 %Chromat. |
3,4,5-trimethoxy-benzaldehyde
isopropyl alcohol
B
3,4,5-trimethoxytoluene
C
(3,4,5-trimethoxyphenyl)methanol
Conditions | Yield |
---|---|
With hydrogenchloride; hydrogen; palladium on activated charcoal at 20℃; under 760.051 Torr; for 7h; | A 6% B 75% C 16% |
3,4,5-Trimethoxybenzyl pivalate
A
3,4,5-trimethoxytoluene
B
Trimethylacetic acid
Conditions | Yield |
---|---|
With N1,N1,N12,N12-tetramethyl-7,8-dihydro-6H-dipyrido[1,2-a:2,1'-c][1,4]diazepine-2,12-diamine In N,N-dimethyl-formamide for 24h; Inert atmosphere; Glovebox; UV-irradiation; | A 11% B 73% |
3,4,5-trimethoxytoluene
Conditions | Yield |
---|---|
With cesium fluoride In N,N,N,N,N,N-hexamethylphosphoric triamide for 0.5h; Ambient temperature; | 71% |
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)nickel (0); 1,1,3,3-Tetramethyldisiloxane; potassium tert-butylate; 1,3-bis(cyclohexyl)imidazolium tetrafluoroborate In toluene at 90℃; for 6h; Glovebox; Inert atmosphere; Sealed tube; | 69% |
With lithium aluminium tetrahydride; hydrogen; palladium on activated charcoal 1.) Et2O; 2.) ethanol, 1 atm; Multistep reaction; | |
Multi-step reaction with 3 steps 1: 86.4 percent / 99 percent N2H4*H2O / methanol / 5 h / Heating 2: 85 percent / K3Fe(CN)6; 25 percent NH4OH / H2O; CH2Cl2 / 4 h / 20 °C 3: 65 percent / Zn-Hg / acetic acid; toluene; H2O / 0.75 h / Heating View Scheme |
methanol
3,4,5-trimethoxy-benzaldehyde
A
3,4,5-trimethoxytoluene
B
3,4,5-trimethoxybenzaldehyde dimethyl acetal
C
1,2,3-trimethoxy-5-(methoxymethyl)benzene
Conditions | Yield |
---|---|
With hydrogenchloride; hydrogen; palladium on activated charcoal at 20℃; under 760.051 Torr; for 0.0833333h; | A 5% B 27% C 65% |
(3,4,5-trimethoxyphenyl)methanol
A
3,4,5-trimethoxytoluene
B
brittonin A
Conditions | Yield |
---|---|
Stage #1: (3,4,5-trimethoxyphenyl)methanol With tert.-butyl lithium In tetrahydrofuran; n-heptane at -78 - 20℃; for 0.333333h; Inert atmosphere; Stage #2: With bis(cyclopentadienyl)titanium dichloride; manganese In tetrahydrofuran for 24h; Inert atmosphere; Reflux; | A 7% B 60% |
With triphenylphosphine In 1,4-dioxane at 200℃; for 16h; Autoclave; Inert atmosphere; | A 54% B 27% |
With bis(cyclopentadienyl)titanium dichloride; manganese In tetrahydrofuran for 1h; Inert atmosphere; Reflux; | A 40% B 14% |
methanol
3,4,5-trimethoxy-benzaldehyde
A
3,4,5-trimethoxytoluene
B
1,2,3-trimethoxy-5-(methoxymethyl)benzene
Conditions | Yield |
---|---|
With hydrogenchloride; hydrogen; palladium on activated charcoal at 20℃; under 760.051 Torr; for 0.133333h; | A 50% B 48% |
With palladium 10% on activated carbon; hydrogen at 20℃; for 3.5h; | A 42 %Spectr. B 58 %Spectr. |
1,2,3-trimethoxy-5-((undecyloxy)methyl)benzene
A
undecyl alcohol
B
3,4,5-trimethoxytoluene
Conditions | Yield |
---|---|
With N1,N1,N12,N12-tetramethyl-7,8-dihydro-6H-dipyrido[1,2-a:2,1'-c][1,4]diazepine-2,12-diamine In N,N-dimethyl-formamide for 72h; Inert atmosphere; Glovebox; UV-irradiation; | A 46% B n/a |
methyl p-toluene sulfonate
3,4,5-trimethoxyphenyl 4-methylbenzenesulfonate
3,4,5-trimethoxytoluene
Conditions | Yield |
---|---|
With 1,1'-bis-(diphenylphosphino)ferrocene; (1,2-dimethoxyethane)dichloronickel(II); tetra-(n-butyl)ammonium iodide; lithium chloride; zinc In N,N-dimethyl acetamide at 40℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; | 40% |
3,4,5-trimethoxybenzyltrimethylammonium iodide
A
3,4,5-trimethoxytoluene
B
brittonin A
Conditions | Yield |
---|---|
With nickel(II) iodide; manganese; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In N,N-dimethyl acetamide at 120℃; for 24h; Inert atmosphere; | A 36% B 15% |
Conditions | Yield |
---|---|
With sodium hydroxide at 70 - 80℃; |
Conditions | Yield |
---|---|
With p-menth-1-ene; palladium on activated charcoal |
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 2h; Heating; Yield given; |
Conditions | Yield |
---|---|
With n-butyllithium 1.) THF, hexane, -78 deg C, 2.) -78 deg C; Yield given. Multistep reaction; |
3,4,5-trimethoxytoluene
2-bromo-3,4,5-trimethoxy-1-methylbenzene
Conditions | Yield |
---|---|
With dihydrogen peroxide; acetic acid; sodium bromide In water at 20℃; for 1h; | 100% |
With sulfuric acid; dihydrogen peroxide; sodium bromide In ethanol at 25℃; for 1h; | 100% |
With dihydrogen peroxide; acetic acid; sodium bromide In water at 40℃; for 2h; | 98.1% |
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate; formic acid In methanol; water at 60℃; for 2.16h; Reagent/catalyst; Temperature; Solvent; | 99% |
Stage #1: 3,4,5-trimethoxytoluene With dihydrogen peroxide; toluene-4-sulfonic acid; acetic acid at 75℃; for 0.5h; Stage #2: With nitric acid In water at 0 - 5℃; for 0.00833333h; | 88% |
With dipotassium peroxodisulfate; formic acid; water at 25℃; for 4h; Reagent/catalyst; | 88% |
3,4,5-trimethoxytoluene
N,N-dimethyl-formamide
2,3,4-trimethoxy-6-methylbenzaldehyde
Conditions | Yield |
---|---|
With trichlorophosphate Vilsmeier-Haack Formylation; | 99% |
With trichlorophosphate at 65℃; for 5h; Vilsmeier-Haack reaction; | 95% |
With trichlorophosphate at 5 - 80℃; for 7h; Vilsmeier-Haack reaction; Inert atmosphere; | 92.4% |
With trichlorophosphate at 90℃; for 1h; | 82.7% |
3,4,5-trimethoxytoluene
2-iodo-3,4,5-trimethoxy-1-methylbenzene
Conditions | Yield |
---|---|
With iodine; silver trifluoroacetate In chloroform at 20℃; for 3h; Inert atmosphere; | 98% |
3,4,5-trimethoxytoluene
5-bromo-2-methoxy-6-methyl-benzoic acid chloride
metrafenone
Conditions | Yield |
---|---|
iron(III) chloride In chlorobenzene at 80℃; for 6h; Friedel Crafts Acylation; | 97.4% |
Conditions | Yield |
---|---|
With hydrogen iodide; hypophosphorous acid Heating; | 96% |
With boron tribromide In dichloromethane at 0 - 25℃; Inert atmosphere; | 59% |
With hydrogen iodide | |
With hydrogen bromide; acetic acid | |
With boron tribromide In dichloromethane at 0℃; for 3h; |
Dichloromethyl methyl ether
3,4,5-trimethoxytoluene
2,3,4-trimethoxy-6-methylbenzaldehyde
Conditions | Yield |
---|---|
With aluminium trichloride In dichloromethane at 25℃; for 2h; | 95% |
With aluminium trichloride In tetrahydrofuran | |
Stage #1: 3,4,5-trimethoxytoluene With aluminum (III) chloride In dichloromethane at 0℃; for 0.75h; Stage #2: Dichloromethyl methyl ether In dichloromethane at 0 - 20℃; |
3,4,5-trimethoxytoluene
2,6-diiodo-3,4,5-trimethoxytoluene
Conditions | Yield |
---|---|
With iodine; periodic acid In acetic acid at 53℃; for 24h; | 93% |
With iodine; periodic acid In acetic acid at 53℃; for 24h; | 93% |
3,4,5-trimethoxytoluene
acetic acid
A
3,4,5-trimethoxybenzyl acetate
B
brittonin A
Conditions | Yield |
---|---|
With nitric acid at 20℃; for 1h; | A 93% B 1% |
Conditions | Yield |
---|---|
With nitric acid at 20℃; for 0.833333h; | 93% |
3,4,5-trimethoxytoluene
A
3,4,5-trimethoxybenzyl acetate
B
3,4,5-trimethoxy-benzaldehyde
Conditions | Yield |
---|---|
With oxygen; cobalt(II) acetate; manganese(II) acetate In acetic acid at 110℃; under 2280 Torr; for 2h; | A 4.2% B 91.2% |
Conditions | Yield |
---|---|
With hydrogenchloride; 1-hexyl-3-methyl-1-imidazolium bromide In water at 80℃; for 6h; chemoselective reaction; | 91% |
formaldehyd
3,4,5-trimethoxytoluene
2-chloromethyl-3,4,5-trimethoxytoluene
Conditions | Yield |
---|---|
With hydrogenchloride In water at 20 - 40℃; for 1h; Blanc Reaction; | 90% |
With hydrogenchloride In water at 35℃; for 1h; Blanc Chloromethylation Reaction; | 85 %Chromat. |
3,4,5-trimethoxytoluene
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; caesium carbonate at 100℃; for 15h; Green chemistry; | 90% |
3,4,5-trimethoxytoluene
Conditions | Yield |
---|---|
With iodobenzene; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; lithium chloride In tetrahydrofuran at 20℃; for 24h; | 89% |
Conditions | Yield |
---|---|
With potassium In tetrahydrofuran for 24h; Ambient temperature; | 87% |
With potassium In tetrahydrofuran for 24h; Ambient temperature; | 87% |
Conditions | Yield |
---|---|
With boron tribromide In dichloromethane at 0℃; for 0.5h; | 87% |
3,4,5-trimethoxytoluene
A
2,6-dibromo-3,4,5-trimethoxytoluene
B
2-bromo-3,4,5-trimethoxy-1-methylbenzene
Conditions | Yield |
---|---|
With bromine; sodium acetate; acetic acid In tetrachloromethane at 10 - 20℃; for 2.5h; Inert atmosphere; | A 11% B 86% |
3,4,5-trimethoxytoluene
1-bromomethyl-3-methoxybenzene
1,2,3-trimethoxy-5-(3-methoxyphenethyl)benzene
Conditions | Yield |
---|---|
Stage #1: 3,4,5-trimethoxytoluene With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; potassium tert-butylate In hexane; n-heptane at 0℃; for 0.25h; Inert atmosphere; Stage #2: 1-bromomethyl-3-methoxybenzene In hexane; n-heptane at 0℃; for 1h; Inert atmosphere; | 86% |
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