Conditions | Yield |
---|---|
With sodium hydrogencarbonate; acrylonitrile; hydroquinone In water at 40 - 67℃; for 5.5h; Reagent/catalyst; Temperature; | 99.05% |
With t-butylnitrite; water; sodium hydrogencarbonate; acrylonitrile at 45 - 67℃; for 3h; Catalytic behavior; Reagent/catalyst; | 99.05% |
With 5,5-Dimethyl-1-pyrroline N-oxide; phenyl tert-butylmethyldimethoxysilane; water; sodium acetate; sodium carbonate; acetonitrile at 45 - 67℃; for 2.5h; Catalytic behavior; Reagent/catalyst; | 99.02% |
2-methylpropenal
cyclohexanol
A
cyclohexanone
B
3-hydroxy-2-methyl-1-propene
Conditions | Yield |
---|---|
With TEMPOL; SnO2#Nb2O5 at 90℃; under 3000.3 Torr; for 10h; Inert atmosphere; | A 95.33% B n/a |
methallyl formate
A
formamide
B
3-hydroxy-2-methyl-1-propene
Conditions | Yield |
---|---|
With aluminum oxide; ammonia at 0 - 5℃; Gas phase; Large scale; | A 850 g B 95% |
Conditions | Yield |
---|---|
With hydrogen In water at 70℃; under 11251.1 Torr; for 1.5h; Temperature; Reagent/catalyst; Pressure; | 94% |
With hydrogen In water at 70℃; under 3000.3 Torr; Temperature; Reagent/catalyst; Pressure; | 89% |
With sodium tetrahydroborate; pyrographite In tetrahydrofuran; water at 20℃; for 0.0166667h; | 85% |
sodium acetate
3-Chloro-2-methylpropene
A
methallyl acetate
B
3-hydroxy-2-methyl-1-propene
Conditions | Yield |
---|---|
With sodium D-gluconate; copper(II) sulfate In water for 4h; Reagent/catalyst; Reflux; | A 92% B 5.5% |
2-methyl-1,2-epoxypropane
A
isobutyraldehyde
B
3-hydroxy-2-methyl-1-propene
Conditions | Yield |
---|---|
lithium phosphate at 210℃; for 3h; Kinetics; Thermodynamic data; 110 - 180 degC , ΔG, ΔH, E(activ.); | A 5.79% B 85.1% |
With hydrogen; lithium phosphate at 210℃; for 3h; | A 5.79% B 85.1% |
With 3-chlorobenzoate; methanesulfonic acid In dichloromethane-d2 at 26.5℃; Product distribution; various conc. of methanesulfonic acid in the presence and absence of 3-chlorobenzoic acid; | A 10% B 20% |
With 3-chlorobenzoate; methanesulfonic acid In dichloromethane-d2 at 26.5℃; | A 10% B 20% |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In diethyl ether at -30℃; for 4h; Reduction; | 83% |
With lithium aluminium tetrahydride In diethyl ether at 0℃; for 1h; | 72% |
3-hydroxy-2-methyl-1-propene
Conditions | Yield |
---|---|
With tellurium; lithium triethylborohydride In tetrahydrofuran for 0.166667h; Ambient temperature; | 70% |
Conditions | Yield |
---|---|
With ZnO/MgZrOx mixed oxide with 4.3 Mg/Zr atomic ratio on MgO nanaosheet at 275℃; Inert atmosphere; | 17% |
2,5-dimethyl-3,4-dihydro-2H-pyran-2-methanol
3-hydroxy-2-methyl-1-propene
Conditions | Yield |
---|---|
With aluminum oxide at 500℃; |
Conditions | Yield |
---|---|
With potassium carbonate |
Conditions | Yield |
---|---|
With aluminum oxide; copper(II) sulfate at 225℃; under 760 Torr; |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride; diethyl ether | |
With diisobutylaluminium hydride In hexane; dichloromethane at -78℃; for 1.5h; Inert atmosphere; |
2-methylpropenal
A
2-methyl-propan-1-ol
B
isobutyraldehyde
C
acetone
D
3-hydroxy-2-methyl-1-propene
Conditions | Yield |
---|---|
With magnesium oxide; isopropyl alcohol; boron trioxide at 270℃; other α,β-unsaturated corbonyl compounds, other alcohols; |
2-methyl-3-prop-2-enyl phenylselenide
3-hydroxy-2-methyl-1-propene
Conditions | Yield |
---|---|
With dihydrogen peroxide In pyridine; dichloromethane at 0℃; for 0.333333h; Yield given; |
methylmagnesium bromide
propargyl alcohol
A
(Z)-(3-<2H>)-2-methylprop-2-en-1-ol
B
3-hydroxy-2-methyl-1-propene
Conditions | Yield |
---|---|
With hydrogenchloride; copper(l) iodide; water-d2 1.) THF, -60 deg C up to RT, 2.) THF, Et2O, H2O, pH=7; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; |
2-methylpropenal
A
2-methyl-propan-1-ol
B
isobutyraldehyde
C
3-hydroxy-2-methyl-1-propene
Conditions | Yield |
---|---|
With hydrogen; AuZr(O) at 89.9℃; Product distribution; pulse reactor; other temperatures; | A 6.7 % Turnov. B 42.9 % Turnov. C 47.2 % Turnov. |
2-chloromethyl-2-methyloxiran
A
1-methylcyclopropanol
B
3-hydroxy-2-methyl-1-propene
Conditions | Yield |
---|---|
With magnesium In tetrahydrofuran Heating; Title compound not separated from byproducts; |
2-(2-methylallyloxy)tetrahydro-2H-pyran
3-hydroxy-2-methyl-1-propene
Conditions | Yield |
---|---|
zeolite HSZ-330 In methanol for 2h; Ambient temperature; |
isobutene
A
3-methyl-butan-2-one
B
acetone
C
3-hydroxy-2-methyl-1-propene
Conditions | Yield |
---|---|
at 200 - 240℃; under 58840.6 Torr; |
3-hydroxy-2-methyl-1-propene
Conditions | Yield |
---|---|
With potassium hydroxide | |
With water; potassium carbonate man destilliert die erhaltene Loesung und Schuettelt das Destillat mit K2CO3, wobei das Isopropenylcarbinol abgeschieden wird, das man ueber CaO entwaessert; |
2-methylpropenal
acetic acid
A
meso-2,5-dimethyl-hexa-1,5-diene-3,4-diol
B
3-hydroxy-2-methyl-1-propene
2-methylpropenal
diethylzinc
A
(R)-3-hydroxy-2-methylpent-1-ene
B
(+)-(R)-2-methylpent-1-en-3-ol
C
3-hydroxy-2-methyl-1-propene
Conditions | Yield |
---|---|
With (1R,2S)-(+)-1-cyclohexyl-2-phenyl-2-(N-morpholino)ethanol In hexane; toluene at 20℃; for 3h; Title compound not separated from byproducts.; |
Conditions | Yield |
---|---|
at 260.4℃; under 49.5 Torr; Kinetics; Further Variations:; Pressures; Temperatures; also in the presence of free radical inhibitors; |
Conditions | Yield |
---|---|
In methanol; potassium hydroxide |
3-[(ethoxycarbonyl)oxy]-2-methylpropyl propanoate
A
propionic acid
B
3-hydroxy-2-methyl-1-propene
Conditions | Yield |
---|---|
at 626.84℃; Kinetics; Further Variations:; Temperatures; |
2-methylallyl 1-naphthyl selenide
A
2-methylpropenal
B
2-bis[3,5bis(trifluoromethyl)phenyl]diselane
C
3-hydroxy-2-methyl-1-propene
Conditions | Yield |
---|---|
With oxygen In n-heptane at 20℃; for 0.25h; Reactivity; Time; UV-irradiation; |
Triethyl orthoacetate
3-hydroxy-2-methyl-1-propene
ethyl 4-methyl-4-pentenoate
Conditions | Yield |
---|---|
With propionic acid for 8h; Reflux; | 100% |
With propionic acid at 118℃; for 6h; Johnson orthoester Claisen rearrangement; | 98% |
With acetic acid at 150 - 170℃; Inert atmosphere; | 87% |
methanesulfonyl chloride
3-hydroxy-2-methyl-1-propene
2-methylallyl methanesulfonate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at -15℃; for 1h; Green chemistry; | 100% |
With triethylamine In tetrahydrofuran for 0.25h; Ambient temperature; | |
With triethylamine In dichloromethane at -20℃; for 1.5h; | |
With triethylamine In diethyl ether at -78 - 0℃; Inert atmosphere; |
Conditions | Yield |
---|---|
With tetrabutylphosphonium peroxotantalate; dihydrogen peroxide In water at 0℃; for 3.5h; Schlenk technique; chemoselective reaction; | 100% |
With C16H36N(1+)*H2NbO5(1-); dihydrogen peroxide In water at 0℃; for 4h; chemoselective reaction; | 96.3% |
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 18h; | 83% |
4-chlorobenzaldehyde
3-hydroxy-2-methyl-1-propene
A
3,3-bis(3-phenyl-2-propen-1-yl)pentane-2,4-dione
B
(E)-1-chloro-4-(3-methylbuta-1,3-dien-1-yl)benzene
Conditions | Yield |
---|---|
With triphenylphosphine; palladium(II) acetylacetonate In 1,4-dioxane for 50h; Heating; | A 100% B 21% C n/a |
p-methoxybenzyl chloride
3-hydroxy-2-methyl-1-propene
1-((methallyloxy)methyl)-4-methoxybenzene
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 20℃; | 100% |
With sodium hydroxide 1.) THF, mineral oil, DMF, 0 deg C, 30 min; 2.) THF, 2 h; | 97% |
With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 0℃; 1.) 30 min, 2.) 2 h; |
Conditions | Yield |
---|---|
With dimesitylammonium pentafluorobenzenesulfonate In n-heptane at 80℃; for 3h; | 100% |
With Iron(III) isopropoxide; zirconium(IV) tetraisopropoxide In n-heptane for 15h; | 99% |
dimesitylammonium pentafluorobenzenesulfonate In n-heptane at 80℃; for 3h; Product distribution / selectivity; | 99% |
[(4-methoxyphenyl)sulfonyl]azanyl sulfamate
3-hydroxy-2-methyl-1-propene
C11H16N2O6S2
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 25℃; Mitsunobu reaction; Cooling with ice; | 100% |
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Mitsunobu reaction; Cooling with ice; | 100% |
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 0 - 20℃; for 20h; | 100% |
Conditions | Yield |
---|---|
Stage #1: N-(p-toluenesulfonyl)aziridine; 3-hydroxy-2-methyl-1-propene In dichloromethane at 0℃; for 0.166667h; Stage #2: With Amberlyst-15 In dichloromethane at 0 - 20℃; for 4h; | 100% |
trichloroacetonitrile
3-hydroxy-2-methyl-1-propene
2-methyl-2-propenyl trichloroacetimidate
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0℃; for 22h; Inert atmosphere; | 99% |
(i) Na, (ii) /BRN= 605572/; Multistep reaction; | |
With sodium hydride In tetrahydrofuran at 0℃; for 2h; | |
With sodium hydride In diethyl ether at 0℃; Esterification; |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; | 99% |
With triethylamine In tetrahydrofuran at 0 - 20℃; for 26h; | 72% |
With pyridine In dichloromethane at 0 - 23℃; for 2.25h; Inert atmosphere; Autoclave; | 70% |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate; acrylonitrile; hydroquinone In water at 40 - 67℃; for 5.5h; Reagent/catalyst; Temperature; | 99.05% |
With t-butylnitrite; water; sodium hydrogencarbonate; acrylonitrile at 45 - 67℃; for 3h; Catalytic behavior; Reagent/catalyst; | 99.05% |
With 5,5-Dimethyl-1-pyrroline N-oxide; phenyl tert-butylmethyldimethoxysilane; water; sodium acetate; sodium carbonate; acetonitrile at 45 - 67℃; for 2.5h; Catalytic behavior; Reagent/catalyst; | 99.02% |
2-methylpropenal
cyclohexanol
A
cyclohexanone
B
3-hydroxy-2-methyl-1-propene
Conditions | Yield |
---|---|
With TEMPOL; SnO2#Nb2O5 at 90℃; under 3000.3 Torr; for 10h; Inert atmosphere; | A 95.33% B n/a |
methallyl formate
A
formamide
B
3-hydroxy-2-methyl-1-propene
Conditions | Yield |
---|---|
With aluminum oxide; ammonia at 0 - 5℃; Gas phase; Large scale; | A 850 g B 95% |
Conditions | Yield |
---|---|
With hydrogen In water at 70℃; under 11251.1 Torr; for 1.5h; Temperature; Reagent/catalyst; Pressure; | 94% |
With hydrogen In water at 70℃; under 3000.3 Torr; Temperature; Reagent/catalyst; Pressure; | 89% |
With sodium tetrahydroborate; pyrographite In tetrahydrofuran; water at 20℃; for 0.0166667h; | 85% |
sodium acetate
3-Chloro-2-methylpropene
A
methallyl acetate
B
3-hydroxy-2-methyl-1-propene
Conditions | Yield |
---|---|
With sodium D-gluconate; copper(II) sulfate In water for 4h; Reagent/catalyst; Reflux; | A 92% B 5.5% |
2-methyl-1,2-epoxypropane
A
isobutyraldehyde
B
3-hydroxy-2-methyl-1-propene
Conditions | Yield |
---|---|
lithium phosphate at 210℃; for 3h; Kinetics; Thermodynamic data; 110 - 180 degC , ΔG, ΔH, E(activ.); | A 5.79% B 85.1% |
With hydrogen; lithium phosphate at 210℃; for 3h; | A 5.79% B 85.1% |
With 3-chlorobenzoate; methanesulfonic acid In dichloromethane-d2 at 26.5℃; Product distribution; various conc. of methanesulfonic acid in the presence and absence of 3-chlorobenzoic acid; | A 10% B 20% |
With 3-chlorobenzoate; methanesulfonic acid In dichloromethane-d2 at 26.5℃; | A 10% B 20% |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In diethyl ether at -30℃; for 4h; Reduction; | 83% |
With lithium aluminium tetrahydride In diethyl ether at 0℃; for 1h; | 72% |
3-hydroxy-2-methyl-1-propene
Conditions | Yield |
---|---|
With tellurium; lithium triethylborohydride In tetrahydrofuran for 0.166667h; Ambient temperature; | 70% |
Conditions | Yield |
---|---|
With ZnO/MgZrOx mixed oxide with 4.3 Mg/Zr atomic ratio on MgO nanaosheet at 275℃; Inert atmosphere; | 17% |
2,5-dimethyl-3,4-dihydro-2H-pyran-2-methanol
3-hydroxy-2-methyl-1-propene
Conditions | Yield |
---|---|
With aluminum oxide at 500℃; |
Conditions | Yield |
---|---|
With potassium carbonate |
Conditions | Yield |
---|---|
With aluminum oxide; copper(II) sulfate at 225℃; under 760 Torr; |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride; diethyl ether | |
With diisobutylaluminium hydride In hexane; dichloromethane at -78℃; for 1.5h; Inert atmosphere; |
2-methylpropenal
A
2-methyl-propan-1-ol
B
isobutyraldehyde
C
acetone
D
3-hydroxy-2-methyl-1-propene
Conditions | Yield |
---|---|
With magnesium oxide; isopropyl alcohol; boron trioxide at 270℃; other α,β-unsaturated corbonyl compounds, other alcohols; |
2-methyl-3-prop-2-enyl phenylselenide
3-hydroxy-2-methyl-1-propene
Conditions | Yield |
---|---|
With dihydrogen peroxide In pyridine; dichloromethane at 0℃; for 0.333333h; Yield given; |
methylmagnesium bromide
propargyl alcohol
A
(Z)-(3-<2H>)-2-methylprop-2-en-1-ol
B
3-hydroxy-2-methyl-1-propene
Conditions | Yield |
---|---|
With hydrogenchloride; copper(l) iodide; water-d2 1.) THF, -60 deg C up to RT, 2.) THF, Et2O, H2O, pH=7; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; |
2-methylpropenal
A
2-methyl-propan-1-ol
B
isobutyraldehyde
C
3-hydroxy-2-methyl-1-propene
Conditions | Yield |
---|---|
With hydrogen; AuZr(O) at 89.9℃; Product distribution; pulse reactor; other temperatures; | A 6.7 % Turnov. B 42.9 % Turnov. C 47.2 % Turnov. |
2-chloromethyl-2-methyloxiran
A
1-methylcyclopropanol
B
3-hydroxy-2-methyl-1-propene
Conditions | Yield |
---|---|
With magnesium In tetrahydrofuran Heating; Title compound not separated from byproducts; |
2-(2-methylallyloxy)tetrahydro-2H-pyran
3-hydroxy-2-methyl-1-propene
Conditions | Yield |
---|---|
zeolite HSZ-330 In methanol for 2h; Ambient temperature; |
isobutene
A
3-methyl-butan-2-one
B
acetone
C
3-hydroxy-2-methyl-1-propene
Conditions | Yield |
---|---|
at 200 - 240℃; under 58840.6 Torr; |
3-hydroxy-2-methyl-1-propene
Conditions | Yield |
---|---|
With potassium hydroxide | |
With water; potassium carbonate man destilliert die erhaltene Loesung und Schuettelt das Destillat mit K2CO3, wobei das Isopropenylcarbinol abgeschieden wird, das man ueber CaO entwaessert; |
1. | skn-rbt 500 mg MOD | SCCUR* Shell Chemical Company. Unpublished Report. (2401 Crow Canyon Rd., San Romon, CA 94583) | ||
2. | orl-mus LDLo:500 mg/kg | SCCUR* Shell Chemical Company. Unpublished Report. (2401 Crow Canyon Rd., San Romon, CA 94583) | ||
3. | ihl-mus LCLo:2924 ppm/2H | SCCUR* Shell Chemical Company. Unpublished Report. (2401 Crow Canyon Rd., San Romon, CA 94583) | ||
4. | skn-rbt LDLo:2000 mg/kg | SCCUR* Shell Chemical Company. Unpublished Report. (2401 Crow Canyon Rd., San Romon, CA 94583) |
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