Conditions | Yield |
---|---|
With palladium dichloride In methanol at 40℃; for 18h; Inert atmosphere; Green chemistry; chemoselective reaction; | 99% |
With [IrCl(CO)(PPh3)2]; hydrazine hydrate; potassium hydroxide In methanol at 160℃; for 3h; Wolff-Kishner Reduction; Sealed tube; | 86% |
With [IrCl(CO)(PPh3)2]; hydrazine hydrate; potassium hydroxide In methanol at 160℃; for 3h; Sealed tube; | 86% |
With carbon monoxide; hydrogen; benzene unter Zusatz von Octacarbonyldikobalt und CoCO3 auf 190grad/238 at; | |
Multi-step reaction with 3 steps 1: 78 percent / sodium iodide; sodium hydride / tetrahydrofuran / 0 - 20 °C 2: sulfuryl chloride / CH2Cl2 / -78 °C 3: lithium; 4,4'-di-tert-butylbiphenyl / tetrahydrofuran / 1 h / 0 °C View Scheme |
4-bromo-3-methylanisole
1-methoxy-3-methyl-benzene
Conditions | Yield |
---|---|
With potassium carbonate; butan-1-ol; palladium diacetate; triphenylphosphine at 100℃; for 14h; | 98% |
3-methoxyphenylacetonitrile
1-methoxy-3-methyl-benzene
Conditions | Yield |
---|---|
Stage #1: 3-methoxyphenylacetonitrile With 15-crown-5; sodium In tetrahydrofuran; hexane at 0℃; for 0.333333h; Birch Reduction; Inert atmosphere; Stage #2: With water In tetrahydrofuran; hexane at 0℃; for 1h; Birch Reduction; Inert atmosphere; chemoselective reaction; | 98% |
Stage #1: 3-methoxyphenylacetonitrile With dibenzo-18-crown-6; sodium In tetrahydrofuran; toluene at 0℃; for 0.333333h; Inert atmosphere; Stage #2: With propan-1-ol In tetrahydrofuran; toluene at 0℃; for 1h; | 78% |
Conditions | Yield |
---|---|
Stage #1: 3-methoxy-benzaldehyde With iron(III) chloride In methanol at 20℃; for 0.05h; Stage #2: In methanol at 20℃; for 0.166667h; chemoselective reaction; | 95% |
With borohydride exchange resin; nickel diacetate In methanol for 3h; Ambient temperature; | 93% |
With triethylsilane; palladium dichloride In ethanol for 0.5h; Inert atmosphere; | 86.0 %Chromat. |
With triethylsilane; palladium dichloride In ethanol at 20℃; for 0.5h; Inert atmosphere; | 86 %Chromat. |
1-iodo-4-methoxy-2-methylbenzene
1-methoxy-3-methyl-benzene
Conditions | Yield |
---|---|
With potassium carbonate; butan-1-ol; palladium diacetate; triphenylphosphine at 100℃; for 1h; | 93% |
Conditions | Yield |
---|---|
With benzyltrimethylammonium chloride; sodium hydroxide In water at 70℃; Concentration; Temperature; Autoclave; | 92.2% |
1-Methoxy-3-methyl-2-(2-methyl-propane-2-sulfonyl)-benzene
1-methoxy-3-methyl-benzene
Conditions | Yield |
---|---|
With bis(acetylacetonate)nickel(II); isopropylmagnesium chloride In tetrahydrofuran at 20℃; for 20h; | 92% |
Conditions | Yield |
---|---|
In methanol for 1.6h; Methylation; | 92% |
Conditions | Yield |
---|---|
With sodium hydroxide at 50℃; for 5h; | 91.8% |
With sodium hydroxide |
Conditions | Yield |
---|---|
With ethene; 5%-palladium/activated carbon at 130℃; under 760.051 Torr; | 88% |
Conditions | Yield |
---|---|
With 20 % Pd(OH)2/C; hydrogen In methanol at 20℃; under 760.051 Torr; for 3h; | 86% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 72℃; for 24h; Inert atmosphere; | 85% |
With sodium hydroxide In N,N-dimethyl acetamide at 25℃; Rate constant; | |
With potassium hydroxide |
Conditions | Yield |
---|---|
With 18-crown-6 ether; potassium carbonate at 150℃; for 2h; | 85% |
Conditions | Yield |
---|---|
With N,N'-dimethylimidazolium-2-carboxylate In acetonitrile at 160℃; for 1.33333h; Microwave irradiation; Green chemistry; | 84% |
With dimanganese decacarbonyl at 180℃; for 1h; Reagent/catalyst; | 81% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 90℃; Inert atmosphere; |
(2R,3S)-2,3-dihydroxy-1-methylcyclohexa-4,6-diene
methyl iodide
A
2-methylmethoxybenzene
C
1-methoxy-3-methyl-benzene
Conditions | Yield |
---|---|
With potassium hydroxide In dimethyl sulfoxide at 0℃; for 1.5h; | A n/a B 80% C n/a |
2-tert-butylsulfinyl-3-methoxytoluene
1-methoxy-3-methyl-benzene
Conditions | Yield |
---|---|
With nickel In ethanol for 8h; Reflux; | 80% |
m-methoxybenzyl chloride
A
1,2-bis(3-methoxyphenyl)ethane
B
1-methoxy-3-methyl-benzene
Conditions | Yield |
---|---|
With nickel In 1,2-dimethoxyethane for 6h; Ambient temperature; | A 69% B n/a |
Conditions | Yield |
---|---|
Stage #1: 3-methoxyphenyl bromide With bis(tri-t-butylphosphine)palladium(0); oxygen In toluene at 20℃; for 0.0166667h; Schlenk technique; Stage #2: methyllithium In toluene at 20℃; for 0.0333333h; Schlenk technique; | 69% |
pentanal
m-methoxyphenylacetic acid
A
1-(3-methoxyphenyl)hexan-2-ol
B
1-methoxy-3-methyl-benzene
Conditions | Yield |
---|---|
With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; caesium carbonate In N,N-dimethyl acetamide at 20℃; for 16h; Irradiation; Inert atmosphere; | A 63% B 20 %Chromat. |
methanol
3-methyl-phenol
A
2,5-Dimethylphenol
B
2,3-Dimethylphenol
C
2,3,6-trimethylphenol
D
1-methoxy-3-methyl-benzene
Conditions | Yield |
---|---|
silica gel at 350℃; under 61504.9 Torr; Product distribution; Further Variations:; Catalysts; Pressures; Temperatures; | A 46% B 9% C 38% D n/a |
2-methoxy-6-methylphenyl trifluoromethanesulfonate
1-methoxy-3-methyl-benzene
Conditions | Yield |
---|---|
With formic acid; tributyl-amine; 1,3-bis-(diphenylphosphino)propane; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 80℃; for 8h; | 46% |
vanillin triflate
A
3-methoxybenzyl alcohol
B
1-methoxy-3-methyl-benzene
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; under 760.051 Torr; for 40h; | A 30% B 42% |
methanol
phenol
A
4-Methylanisole
B
2-methylmethoxybenzene
C
2-methoxy-1,3-dimethylbenzene
D
2,4-dimethylanisole
E
methoxybenzene
F
1-methoxy-3-methyl-benzene
Conditions | Yield |
---|---|
APTi-II-770 at 349.9℃; Product distribution; alkylation; other catalysts, other temperatures; also cresols, further products; | A n/a B 1.8% C n/a D n/a E 19% F n/a |
4,4',4''-((1,3,5-triazine-2,4,6-triyl)tris(oxy))tris(3-methoxybenzaldehyde)
1-methoxy-3-methyl-benzene
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 24h; | 14% |
Conditions | Yield |
---|---|
With water; tris-(dibenzylideneacetone)dipalladium(0); trifuran-2-yl-phosphane In tetrahydrofuran Heating; | 3% |
Conditions | Yield |
---|---|
With diethyl ether; magnesium anschliessend Behandeln mit Dimethylsulfat, zuletzt auf dem Dampfbad; |
diethyl ether
2-bromo-3-methylanisole
lithium dimethylamide
B
1-methoxy-3-methyl-benzene
2,4-dibromo-5-methylanisole
A
4-bromo-3-methylanisole
B
1-methoxy-3-methyl-benzene
Conditions | Yield |
---|---|
With diethyl ether; magnesium anschliessende Hydrolyse; |
Conditions | Yield |
---|---|
at 400 - 420℃; durch Ueberleiten ueber ThO2; |
1-methoxy-3-methyl-benzene
4-bromo-3-methylanisole
Conditions | Yield |
---|---|
With hydrogenchloride; N-Bromosuccinimide; water In acetone at 20℃; for 0.0833333h; Inert atmosphere; | 100% |
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; methyl 2-n-pentyl-1H-indole-3-carboxylate In n-heptane at 23℃; for 16h; Darkness; Green chemistry; regioselective reaction; | 99% |
With N-Bromosuccinimide; 2,4,6-trimethylaniline In dichloromethane at -40℃; for 2h; Inert atmosphere; regioselective reaction; | 98% |
1-methoxy-3-methyl-benzene
1-iodo-4-methoxy-2-methylbenzene
Conditions | Yield |
---|---|
With iodine; n-butyltriphenylphosphonium peroxodisulfate In acetonitrile for 0.5h; Heating; | 100% |
With N,N,N-trimethylbenzenemethanaminium dichloroiodate; zinc(II) chloride In acetic acid for 0.5h; Ambient temperature; | 94% |
With N-iodo-succinimide; 2,4,6-trifluoroaniline In dichloromethane at 20℃; for 24h; Inert atmosphere; regioselective reaction; | 94% |
1-methoxy-3-methyl-benzene
Conditions | Yield |
---|---|
Stage #1: 1-methoxy-3-methyl-benzene With potassium tert-butylate at -35℃; for 0.333333h; Stage #2: With n-butyllithium In hexane at -35 - 20℃; for 12h; | 100% |
1-methoxy-3-methyl-benzene
2-bromo-5-methoxybenzyl bromide
Conditions | Yield |
---|---|
With N-Bromosuccinimide In dichloromethane for 4h; Heating; IR lamp; | 99% |
With N-Bromosuccinimide In dichloromethane for 4h; Bromination; Heating; irradiation; | 88% |
With N-Bromosuccinimide Photolysis; | 88% |
4-methyl-1,2,4-triazoline-3,5-dione
1-methoxy-3-methyl-benzene
1-(4-methoxy-2-methylbenzene)-4-methyl-1,2,4-triazoline-3,5-dione
Conditions | Yield |
---|---|
With trifluoroacetic acid In chloroform at 62℃; for 0.166667h; regioselective reaction; | 99% |
Conditions | Yield |
---|---|
With tetrabutylammonium acetate for 4.5h; Electrolysis; Inert atmosphere; Sealed tube; regioselective reaction; | 99% |
Conditions | Yield |
---|---|
In dichloromethane at 20℃; | 98% |
1-methoxy-3-methyl-benzene
A
3-methylcyclohexen-2-one
B
3-Methylcyclohexanone
Conditions | Yield |
---|---|
With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium In tetrahydrofuran; ethanol at -30℃; for 2h; | A 97% B 3% |
1-methoxy-3-methyl-benzene
1-chloro-4-methoxy-2-methylbenzene
Conditions | Yield |
---|---|
With N-chloro-succinimide; 2,4,6-trimethylaniline In dichloromethane at 20℃; Inert atmosphere; regioselective reaction; | 96% |
With aluminum oxide; sodium chlorite; (salen)Mn(III) In dichloromethane at 20℃; for 0.5h; | 87% |
With Oxone; potassium chloride In water; acetonitrile at 20℃; | 76% |
1-methoxy-3-methyl-benzene
2,4-diiodo-5-methyl-methoxybenzene
Conditions | Yield |
---|---|
With N,N,N-trimethylbenzenemethanaminium dichloroiodate; zinc(II) chloride In acetic acid for 24h; Ambient temperature; | 96% |
With iodine; mercury(II) oxide In dichloromethane for 20h; Ambient temperature; | 80% |
With sulfuric acid; iodine; periodic acid In water; acetic acid |
1-methoxy-3-methyl-benzene
1-deuteriomethyl-3-methoxybenzene
Conditions | Yield |
---|---|
Stage #1: 1-methoxy-3-methyl-benzene With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; potassium tert-butylate In tetrahydrofuran; hexane at -78℃; Inert atmosphere; Stage #2: With d(4)-methanol In tetrahydrofuran; hexane Inert atmosphere; regioselective reaction; | 96% |
1-methoxy-3-methyl-benzene
3-methoxybenzyl 3-methoxybenzoate
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In water at 80℃; for 6h; | 96% |
Conditions | Yield |
---|---|
With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydride; N-methylaniline In diethyl ether; xylene at 120℃; for 6.5h; | 95% |
With trimethylsilyl iodide at 105 - 114℃; for 0.25h; Microwave irradiation; Inert atmosphere; | 92% |
With 1,3-dimethyl-2-imidazolidinone; sodium hexamethyldisilazane In tetrahydrofuran at 185℃; for 12h; further reagent: LDA; | 87% |
Conditions | Yield |
---|---|
In methanol; water at 20℃; for 2h; | 95% |
With trifluoroacetic acid |
1-methoxy-3-methyl-benzene
[(2,6-bis(diphenylphosphinomethyl)pyridine)Pt(C2H4C6H3(OMe)Me)]SbF6
[(2,6-bis(diphenylphosphinomethyl)pyridine)Pt(C2H4C6H3(OMe)Me)]SbF6
Conditions | Yield |
---|---|
In dichloromethane; water aryl compd. (1.5 equiv.) and H2O were added to soln. of Pt complex in CH2Cl2; mixt. was stirred for 2 h; dried (Na2SO4); filtered; concd. (vac.); Et2O added dropwise; filtered; dried (vac.); elem. anal.; | A 95% B n/a |
1-methoxy-3-methyl-benzene
Conditions | Yield |
---|---|
With iron(III) chloride; silver hexafluoroantimonate In 1,2-dichloro-ethane at 100℃; for 16h; Inert atmosphere; Sealed tube; | 95% |
tertiary butyl chloride
1-methoxy-3-methyl-benzene
2-tert-butyl-5-methylanisole
Conditions | Yield |
---|---|
rhenium(I) pentacarbonyl bromide In 1,2-dichloro-ethane at 84℃; for 5h; Product distribution; | 93% |
Stage #1: 1-methoxy-3-methyl-benzene With aluminum (III) chloride In dichloromethane at 0 - 5℃; for 1h; Stage #2: tertiary butyl chloride In dichloromethane at 0 - 5℃; for 5h; Temperature; | 87.46% |
With phosphoric acid at 55 - 60℃; | |
With aluminium trichloride | |
With aluminium trichloride |
Conditions | Yield |
---|---|
With [2,2]bipyridinyl; ammonia; dihydrogen peroxide; oxygen In N,N-dimethyl-formamide at 80℃; under 1500.15 - 3000.3 Torr; for 6h; Autoclave; | 93% |
With tert.-butylnitrite; N-hydroxyphthalimide; palladium diacetate In acetonitrile at 70℃; for 24h; Inert atmosphere; Sealed tube; | 81% |
With air; ammonia; vanadium-titanium oxide at 383.9℃; for 0.000333333h; | 16.1 |
Conditions | Yield |
---|---|
Stage #1: dicyanozinc; 1-methoxy-3-methyl-benzene With hydrogenchloride In 1,1,2,2-tetrachloroethane at 17℃; Stage #2: With aluminium trichloride In 1,1,2,2-tetrachloroethane at 55℃; for 3h; | 93% |
(E)-3-phenylacrylic acid
1-methoxy-3-methyl-benzene
A
3-(4-hydroxy-2-methyl-phenyl)-3-phenyl-propionic acid
B
3-(4-methoxy-2-methyl-phenyl)-3-phenyl-propionic acid
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid at 125℃; for 3h; | A 5% B 93% |
1-diacetoxy-2-methoxyphenyl-λ3-iodane
trifluoroacetic acid
1-methoxy-3-methyl-benzene
Conditions | Yield |
---|---|
In dichloromethane at -30 - 20℃; | 93% |
1-methoxy-3-methyl-benzene
4-hydroxy-3-methyl-cyclohex-2-en-1-one
Conditions | Yield |
---|---|
Stage #1: 1-methoxy-3-methyl-benzene With ammonia; lithium; tert-butyl alcohol In diethyl ether at -78℃; Birch reduction; Inert atmosphere; Stage #2: With oxalic acid In methanol; water at 20℃; for 1h; Stage #3: With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 3h; Inert atmosphere; | 93% |
para-methylphenylmagnesium bromide
1-methoxy-3-methyl-benzene
3,4'-dimethylbiphenyl
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)nickel (0); C23H28N4 In tetrahydrofuran; m-xylene at 60℃; for 4h; Kumada Cross-Coupling; Inert atmosphere; Sealed tube; | 93% |
With (IPr)Ni(π-allyl)Cl In tetrahydrofuran at 60℃; for 12h; Kumada Cross-Coupling; Inert atmosphere; | 81% |
1-methoxy-3-methyl-benzene
1-methoxy-5-methyl-cyclohexa-1,4-diene
Conditions | Yield |
---|---|
With lithium In ethanol; ammonia at -78℃; for 0.5h; | 92% |
With ammonia; sodium In diethyl ether at -78 - -35℃; for 2h; | 82% |
With ammonia; sodium In diethyl ether; tert-butyl alcohol at -78 - -35℃; for 2h; | 82% |
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