Conditions | Yield |
---|---|
With formic acid; palladium and silver nanoparticles over graphitic carbon nitride surface In water at 20℃; for 4h; Catalytic behavior; Reagent/catalyst; Temperature; Sealed tube; Irradiation; | 100% |
With hydrogen; acetic acid; palladium on activated charcoal at 55℃; for 24h; | 99% |
With hydrogen In water at 150℃; under 3750.38 Torr; for 5h; Reagent/catalyst; Temperature; Pressure; Time; Solvent; Autoclave; | 99.8% |
Conditions | Yield |
---|---|
With hydrogen In water at 70℃; Catalytic behavior; | A 99.9% B n/a |
With hydrogen In water at 20 - 100℃; under 3750.38 Torr; for 1h; Kinetics; Reagent/catalyst; Temperature; Pressure; Autoclave; | A 90.9% B 9.1% |
With 2 wt% Pd/C; hydrogen In water at 20 - 100℃; under 3750.38 Torr; for 1h; Kinetics; Reagent/catalyst; Autoclave; | A 21.8% B 78.3% |
Conditions | Yield |
---|---|
With Methyl formate; copper(l) chloride In methanol at 110℃; for 2h; Autoclave; | 98% |
In methanol at 200℃; under 120012 Torr; for 0.0333333h; Temperature; Pressure; Time; Autoclave; | 13.38 g |
Conditions | Yield |
---|---|
Stage #1: 4-hydroxymethyl-2-methoxyphenol With ammonium formate In ethanol; water at 22℃; for 0.166667h; Stage #2: With formic acid In ethanol; water at 22℃; for 1h; Catalytic behavior; Reagent/catalyst; Temperature; Solvent; chemoselective reaction; | 95% |
With lithium aluminium tetrahydride In tetrahydrofuran; chlorobenzene for 3h; Heating; | 87% |
With triethylsilane; palladium dichloride In ethanol at 20℃; for 0.166667h; Inert atmosphere; | 96 %Chromat. |
1-(allyloxy)-2-methoxy-4-methylbenzene
2-Methoxy-4-methylphenol
Conditions | Yield |
---|---|
Stage #1: 1-(allyloxy)-2-methoxy-4-methylbenzene With tert.-butyl lithium In diethyl ether; pentane at -78℃; for 2h; Inert atmosphere; Stage #2: With methanol In diethyl ether; pentane at -78℃; Inert atmosphere; | 88% |
Conditions | Yield |
---|---|
Stage #1: 4-hydroxy-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; Stage #3: With hydrogenchloride In water pH=1; chemoselective reaction; | 84% |
Stage #1: 4-hydroxy-3-methoxyphenylacetonitrile With 15-crown-5; sodium In tetrahydrofuran; hexane at 0℃; for 0.333333h; Inert atmosphere; Stage #2: With water In tetrahydrofuran; hexane at 0℃; for 1h; | 74% |
1-methoxy-3-methyl-benzene
A
2-Methoxy-4-methylphenol
B
1-hydroxy-4-methoxy-2-methylbenzene
C
2-methyl-6-methoxyphenol
Conditions | Yield |
---|---|
With wild type cytochrome P450 CYP102A1 variants RLYF/A330P; oxygen; NADPH Reagent/catalyst; Enzymatic reaction; | A 11% B 80% C 7% |
2-Methoxy-4-methylphenol
Conditions | Yield |
---|---|
With chlorobis(ethylene)rhodium(I) dimer; hydrogen In 1,4-dioxane at 150℃; under 7757.43 Torr; Pressure; Reagent/catalyst; | 79% |
Propionic acid 2-methoxy-4-methyl-phenyl ester
A
2-Methoxy-4-methylphenol
B
hydroxy-5 methoxy-4 methyl-2 propiophenone
C
propionyloxy-5 methoxy-4 methyl-2 propiophenone
Conditions | Yield |
---|---|
With aluminium trichloride In dichloromethane at 20℃; for 8h; | A 32% B 59% C 4% |
With aluminium trichloride In dichloromethane at 0℃; for 8h; | A 32% B 49% C 20% |
Conditions | Yield |
---|---|
Stage #1: 2-(2-methoxy-4-methylphenoxy)acetic acid With diphenyl-phosphinic acid; triethylamine In N,N-dimethyl-formamide; toluene for 3h; Curtius-rearrangement; Heating; Stage #2: With water In N,N-dimethyl-formamide; toluene Heating; Further stages.; | 59% |
Conditions | Yield |
---|---|
With hydrogen In water at 100℃; under 15001.5 Torr; for 3h; Autoclave; | A 6.9% B 53.7% |
With isopropyl alcohol at 140℃; for 15h; Reagent/catalyst; Autoclave; |
2,4'-dimethoxy-4-methyldiphenyl ether
sodium methylate
A
2-Methoxy-4-methylphenol
B
1,1,4,4-tetramethoxycyclohexa-2,5-diene
Conditions | Yield |
---|---|
In methanol anodic oxidation; Pt foil anode and catode; | A n/a B 53% |
4-hydroxymethyl-2-methoxyphenol
A
2-Methoxy-4-methylphenol
B
4,4’-dihydroxy-3,3’-dimethoxybibenzyl
Conditions | Yield |
---|---|
With triphenylphosphine In 1,4-dioxane at 200℃; for 16h; Autoclave; Inert atmosphere; | A 33% B 53% |
vanillin
A
p-cresol
B
2-Methoxy-4-methylphenol
C
4-hydroxymethyl-2-methoxyphenol
Conditions | Yield |
---|---|
With hydrogen In water at 100℃; under 15001.5 Torr; for 3h; Autoclave; | A 6.9% B 52.3% C 6.63% |
With hydrogen In water at 100℃; under 15001.5 Torr; for 3h; Autoclave; | A 6.9% B 52.9% C 6.9% |
With hydrogen In water at 100℃; under 15001.5 Torr; for 3h; Autoclave; | A 5.3% B 49.9% C 11.8% |
1,2-dimethoxy-4-methylbenzene
A
5-methyl-2-methoxyphenol
B
2-Methoxy-4-methylphenol
C
4-methyl-1,2-dihydroxybenzene
Conditions | Yield |
---|---|
With orcinol; Acetobacterium dehalogenans veratrol-O-demethylase; Desulfitobacterium hafniense methyltransferase dhaf4611 In aq. buffer at 25℃; for 24h; pH=6.5; Inert atmosphere; Enzymatic reaction; regioselective reaction; | A 35% B 52% C 13% |
3,3'-dimethoxy-5,5'-dimethyl-[1,1'-biphenyl]-2,2'-diol
2-Methoxy-4-methylphenol
Conditions | Yield |
---|---|
Stage #1: 3,3'-dimethoxy-5,5'-dimethyl-[1,1'-biphenyl]-2,2'-diol With Chlorodiisopropylphosphane; sodium hydride In 1,4-dioxane at 20℃; Stage #2: With chlorobis(ethylene)rhodium(I) dimer; hydrogen In 1,4-dioxane at 150℃; under 2585.81 Torr; | 50% |
Multi-step reaction with 2 steps 1: triethylamine 2: hydrogen; chlorobis(ethylene)rhodium(I) dimer / 1,4-dioxane / 150 °C / 7757.43 Torr View Scheme |
2-methoxy-p-tolyl acetate
A
2-Methoxy-4-methylphenol
B
hydroxy-5 methoxy-4 methyl-2 acetophenone
C
acetoxy-5 methoxy-4 methyl-2 acetophenone
Conditions | Yield |
---|---|
With aluminium trichloride In dichloromethane at 0℃; for 8h; | A 32% B 45% C 15% |
2-methoxy-4-methylphenoxybenzene
A
2-Methoxy-4-methylphenol
B
cyclohexane
C
methyl cyclohexane
Conditions | Yield |
---|---|
With hydrogen In decalin at 200℃; under 75007.5 Torr; for 3h; | A 45% B n/a C n/a |
Conditions | Yield |
---|---|
Stage #1: allyl 2-bromo-6-methoxy-4-methylphenyl ether With tert.-butyl lithium In diethyl ether; pentane at -78℃; Inert atmosphere; Stage #2: With N,N,N,N,-tetramethylethylenediamine In diethyl ether; pentane at -78 - 0℃; Inert atmosphere; Stage #3: With water Inert atmosphere; | A 35% B 42% |
3,3'-dimethoxy-5,5'-dimethyl-[1,1'-biphenyl]-2,2'-diol
A
2-Methoxy-4-methylphenol
B
5,5'-Dimethyl-1,1'-biphenyl-2,2',3,3'-tetrol
C
2-methoxy-phenol
Conditions | Yield |
---|---|
With sulfuric acid; water at 224.84℃; under 21752.2 Torr; for 1.5h; Inert atmosphere; Autoclave; | A 7% B 9% C 12% D 42% |
vanillin
A
2-Methoxy-4-methylphenol
B
5-[(4-hydroxy-3-methoxyphenyl)methyl]-2-methoxy-4-methylphenol
Conditions | Yield |
---|---|
With triethylsilane; zinc(II) iodide In 1,2-dichloro-ethane at 20℃; for 7h; | A 28% B 34% |
Conditions | Yield |
---|---|
With Pd-BaSO4; ethyl acetate Hydrogenation; |
Conditions | Yield |
---|---|
With potassium hydroxide at 150 - 155℃; under 11032.6 Torr; |
5-bromo-2-methoxy-4-methylphenol
2-Methoxy-4-methylphenol
pinoresinol
A
2-Methoxy-4-methylphenol
B
2-methoxy-4-propenylphenol
C
2-methoxy-phenol
Conditions | Yield |
---|---|
Bei der trockenen Destillation; |
Conditions | Yield |
---|---|
With palladium on activated charcoal; acetic acid Hydrogenation; |
Conditions | Yield |
---|---|
With alkali at 50 - 60℃; |
sodium methyl sulfate
4-methyl-1,2-dihydroxybenzene
A
2-Methoxy-4-methylphenol
B
1,2-dimethoxy-4-methylbenzene
Conditions | Yield |
---|---|
With potassium hydroxide |
Conditions | Yield |
---|---|
With sulfuric acid at 0℃; for 24h; Mechanism; Irradiation; | 7.9 % Chromat. |
3-methoxy-4-nitrotoluene
A
2-Methoxy-4-methylphenol
B
2-nitro-5-methylphenol
Conditions | Yield |
---|---|
With sodium hydroxide; tert-butyl alcohol In water Quantum yield; Irradiation; |
2-Methoxy-4-methylphenol
allyl bromide
1-(allyloxy)-2-methoxy-4-methylbenzene
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 12h; Heating; | 100% |
With potassium carbonate; sodium iodide In acetone for 15h; Reflux; Inert atmosphere; | 96% |
With potassium carbonate In acetone for 6h; Heating; | 95% |
formaldehyd
2-Methoxy-4-methylphenol
dimethyl amine
6<(dimethylamino)methyl>-2-methoxy-4-methylphenol
Conditions | Yield |
---|---|
In water for 1.5h; | 100% |
Conditions | Yield |
---|---|
With pyridine; copper(I) bromide dimethylsulfide complex; sodium carbonate In acetonitrile at 75℃; for 48h; Inert atmosphere; solid phase reaction; | 100% |
Conditions | Yield |
---|---|
With perchloric acid; d(4)-methanol at 75℃; for 96h; Inert atmosphere; | 100% |
With sulfuryl dichloride; water-d2 at 100℃; for 30h; Microwave irradiation; Sealed tube; | 100 %Chromat. |
Conditions | Yield |
---|---|
With hydrogenchloride In water at 250℃; under 37503.8 Torr; for 3h; Autoclave; Inert atmosphere; Green chemistry; | 99% |
With aluminium(III) iodide; tetra-(n-butyl)ammonium iodide In cyclohexane for 0.7h; Heating; | 98% |
With aluminium(III) iodide In dimethyl sulfoxide; acetonitrile at 80℃; for 18h; | 96% |
Conditions | Yield |
---|---|
With zirconium(IV) chloride at 20℃; for 0.25h; | 99% |
With sulfuric acid | |
With sulfuric acid at 100℃; |
Conditions | Yield |
---|---|
With triethylamine In hexane; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran | 99% |
trifluoromethylsulfonic anhydride
2-Methoxy-4-methylphenol
2-methoxy-4-methylphenyl trifluoromethanesulfonate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at -78 - 20℃; for 14h; Inert atmosphere; | 99% |
Stage #1: 2-Methoxy-4-methylphenol With pyridine In dichloromethane at 0℃; for 0.0833333h; Inert atmosphere; Schlenk technique; Stage #2: trifluoromethylsulfonic anhydride In dichloromethane at 0 - 20℃; for 18h; Inert atmosphere; Schlenk technique; | 78% |
2-Methoxy-4-methylphenol
4-fluorobenzonitrile
4-(2-methoxy-4-methylphenoxy)benzonitrile
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl acetamide at 100℃; for 30h; | 99% |
2-Methoxy-4-methylphenol
2-fluorobenzonitrile
2-(2-methoxy-4-methyl-phenoxy)-benzonitrile
Conditions | Yield |
---|---|
With caesium carbonate In dimethyl amine at 100℃; for 30h; | 99% |
titanium(IV) isopropylate
2-Methoxy-4-methylphenol
[(2-methoxy-4-methylphenoxy)2Ti(isopropoxy)2]
Conditions | Yield |
---|---|
In cyclohexane at 20℃; Inert atmosphere; Schlenk technique; | 99% |
2-Methoxy-4-methylphenol
carbon dioxide
2-hydroxy-3-methoxy-5-methylbenzoic acid
Conditions | Yield |
---|---|
Stage #1: 2-Methoxy-4-methylphenol; carbon dioxide With potassium carbonate at 200℃; under 41372.9 Torr; for 4.5h; Kolbe-Schmitt reaction; Autoclave; Stage #2: With hydrogenchloride In water at 20℃; pH=1; | 98% |
With potassium carbonate at 200℃; under 41371.8 Torr; for 4h; Carboxylation; Kolbe-Schmitt carboxylation; |
Conditions | Yield |
---|---|
With [bis(acetoxy)iodo]benzene at 20℃; for 1h; | 98% |
2-Methoxy-4-methylphenol
trimethylsilylazide
(4-methyl-2-methoxyphenoxy)trimethylsilane
Conditions | Yield |
---|---|
tetrabutylammomium bromide at 30℃; for 4h; | 98% |
Conditions | Yield |
---|---|
With dmap In tetrahydrofuran Heating; | 98% |
2-Methoxy-4-methylphenol
benzyl bromide
1-(benzyloxy)-2-methoxy-4-methylbenzene
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile for 18h; Reflux; | 98% |
With potassium carbonate In acetonitrile for 18h; Reflux; | 98% |
With potassium carbonate In acetone at 50℃; for 12h; Inert atmosphere; | 96% |
Stage #1: 2-Methoxy-4-methylphenol With sodium hydride In DMF (N,N-dimethyl-formamide) at 0℃; for 0.5h; Stage #2: benzyl bromide With tetrabutylammomium bromide In DMF (N,N-dimethyl-formamide) at 0 - 20℃; |
1-bromo-4-butene
2-Methoxy-4-methylphenol
1-(but-3-enyloxy)-2-methoxy-4-methylbenzene
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile for 12h; Reflux; | 98% |
Conditions | Yield |
---|---|
With iron(III) chloride; di-tert-butyl peroxide; trifluoroacetic acid at 20℃; for 24h; chemoselective reaction; | 98% |
With 1,1,1,3',3',3'-hexafluoro-propanol; periodic acid In nitromethane; N,N-dimethyl-formamide at 20℃; for 0.5h; | 34% |
formaldehyd
2-Methoxy-4-methylphenol
2,2'-dihydroxy-3,3'-dimethoxy-5,5'-dimethyl-diphenylmethane
Conditions | Yield |
---|---|
With sodium hydroxide for 2.5h; Dimerization; | 97% |
With zinc(II) acetate dihydrate for 16h; Inert atmosphere; Reflux; regioselective reaction; | 41% |
With zinc(II) acetate dihydrate for 16h; Reflux; Inert atmosphere; | 41% |
With zinc diacetate |
2-Methoxy-4-methylphenol
Conditions | Yield |
---|---|
With copper diacetate; ethylene glycol at 75℃; for 12h; Green chemistry; | 97% |
2-Methoxy-4-methylphenol
N-[(trifluoromethyl)sulfanyl]aniline
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid In dichloromethane at 20℃; regioselective reaction; | 97% |
Conditions | Yield |
---|---|
Stage #1: 2-Methoxy-4-methylphenol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Sealed tube; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 60℃; Sealed tube; | 96% |
With sodium hydroxide In N,N-dimethyl acetamide at 25℃; Rate constant; |
Conditions | Yield |
---|---|
With [bis(acetoxy)iodo]benzene at 20℃; Diels-Alder reaction; | 96% |
With isosorbide dinitrate | 88% |
Conditions | Yield |
---|---|
With nitronium tetrafluoborate; oxygen In sulfolane at 20℃; for 24h; Sealed tube; | 96% |
2-Methoxy-4-methylphenol
propionyl chloride
hydroxy-5 methoxy-4 methyl-2 propiophenone
Conditions | Yield |
---|---|
With aluminium trichloride In dichloromethane at 20℃; for 2h; | 95% |
2-Methoxy-4-methylphenol
N,N-diethylcarbamyl chloride
N,N-diethyl-1-carbamyloxy-2-methoxy-4-methylbenzene
Conditions | Yield |
---|---|
Stage #1: 2-Methoxy-4-methylphenol With sodium hydride In tetrahydrofuran at 20℃; for 2h; Stage #2: N,N-diethylcarbamyl chloride In tetrahydrofuran at 20℃; for 8h; | 95% |
With sodium hydride In tetrahydrofuran at 20℃; | 95% |
1. | sce-hmn:lyms 500 µmol/L | MUREAV Mutation Research. 206 (1988),17. | ||
2. | orl-rat LD50:740 mg/kg | FOMDAK Folia Medica. 32 (1991),309. | ||
3. | ivn-mus LD50:76 mg/kg | AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. 164 (1966),30. |
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