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1,1-dimethyl-trimethylene carbonate
A
methanol
B
3-methyl-butane-1,3-diol
Conditions | Yield |
---|---|
With C23H21MnN2O3P(1+)*Br(1-); potassium tert-butylate; hydrogen In 1,4-dioxane at 140℃; under 37503.8 Torr; for 16h; Autoclave; | A 99 %Chromat. B 99% |
1,1-dimethyl-trimethylene carbonate
3-methyl-butane-1,3-diol
Conditions | Yield |
---|---|
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); potassium tert-butylate; hydrogen In tetrahydrofuran at 140℃; under 38002.6 Torr; for 12h; Autoclave; | 97% |
3-methyl-butane-1,3-diol
Conditions | Yield |
---|---|
With sodium tetrachloroaurate(III) dihydrate In methanol at 20℃; for 40h; | 93% |
Conditions | Yield |
---|---|
In tetrahydrofuran; diethyl ether at 0℃; for 1h; Grignard reaction; | 64% |
formaldehyd
isobutene
A
4-methyl-3,6-dihydro-2H-pyran
B
4-methyl-3,4-dihydro-2H-pyran
C
3-methyl-butane-1,3-diol
D
methylcyclopentadiene
E
3,4,4-trimethylcyclohexene
F
isovaleraldehyde
G
isoprene
Conditions | Yield |
---|---|
With niobium phosphate at 299.84℃; for 3.33333h; Temperature; | A n/a B n/a C n/a D n/a E n/a F n/a G 57% |
Conditions | Yield |
---|---|
With magnesium Grignard reaction; | 50% |
ethyl 3-hydroxy-3-methylbutanoate
3-methyl-butane-1,3-diol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride | 40% |
With lithium aluminium tetrahydride In diethyl ether | |
With lithium aluminium tetrahydride |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 3h; | 39% |
Conditions | Yield |
---|---|
With methanol; sulfuric acid | |
With water; chlorine at 2 - 8℃; | |
With ion-exchange resin + form>; ethanethiol In 1,4-dioxane | |
With europium(III) hydroxide; water at 180℃; for 9h; Autoclave; | |
With ethanol; sulfuric acid bei Siedetemperatur; |
Conditions | Yield |
---|---|
at 150℃; |
Conditions | Yield |
---|---|
With potassium carbonate | |
With potassium carbonate | |
With sodium hydroxide at 150℃; |
1,3-dibromo-3-methylbutane
3-methyl-butane-1,3-diol
Conditions | Yield |
---|---|
With potassium carbonate |
Conditions | Yield |
---|---|
With sulfuric acid at 25℃; |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride; diethyl ether |
Conditions | Yield |
---|---|
With methanol; sodium methylate |
formaldehyd
isobutene
A
4,4-dimethyl-1,3-dioxane
B
3-methyl-butane-1,3-diol
Conditions | Yield |
---|---|
With boron trifluoride | |
With water at 135℃; for 3h; Reagent/catalyst; Temperature; Autoclave; | A 23 %Chromat. B 70 %Chromat. |
Conditions | Yield |
---|---|
With sulfuric acid at 25℃; Rate constant; Thermodynamic data; effective energy of activation; | |
With sulfuric acid | |
With sodium hydroxide; sodium tetrahydroborate; mercury(II) diacetate; water 1.) tetrahydrofuran, 1 h, 2.) 25 deg C, 3 h; Yield given. Multistep reaction; |
4,4-dimethyl-1,3-dioxane
acetaldehyde
A
3-methyl-butane-1,3-diol
B
2,4,4-trimethyl-1,3-dioxane
Conditions | Yield |
---|---|
sulfuric acid In hexane at 70℃; Product distribution; var. time; |
4,4-dimethyl-1,3-dioxane
A
4-methyl-3,6-dihydro-2H-pyran
B
2-methyl-1-buten-4-ol
C
3-methyl-butane-1,3-diol
D
4-hydroxy-4-methyltetrahydropyran
E
2-methyl-3-buten-2-ol
F
3-methyl-2-buten-1-ol
Conditions | Yield |
---|---|
With sulfuric acid at 120℃; for 3h; Product distribution; various catalyst, various temperature, various time, extent of conversion, solvent cyclohexane; |
Conditions | Yield |
---|---|
With water In isopropyl alcohol at 60℃; Rate constant; Mechanism; Equilibrium constant; other solvent and temperature ; ΔH(excit.), ΔS(excit.); energy of activation; | |
With sulfuric acid; water In water at 25℃; Thermodynamic data; Equilibrium constant; Mechanism; E(activ.), various acid catalysts, acid concentrations, temperatures; |
1-tert-butoxy-3-methyl-3-butanol
A
3-methyl-butane-1,3-diol
B
tert-butyl alcohol
Conditions | Yield |
---|---|
With sulfuric acid at 40℃; Kinetics; Rate constant; Equilibrium constant; var. temperatures; energy data: E, log A; |
acetaldehyde
isobutene
A
4,4-dimethyl-1,3-dioxane
B
2,4,4,6-tetramethyl-1,3-dioxane
C
2-methyl-2,4-pentanediol
D
3-methyl-butane-1,3-diol
E
2,4,4-trimethyl-1,3-dioxane
Conditions | Yield |
---|---|
With formaldehyd; sulfuric acid In various solvent(s) at 70℃; for 4.33333h; Product distribution; var. time, steel bomb; | A 5.6 mmol B 8.5 mmol C n/a D n/a E 16.4 mmol |
2,4,4-trimethyl-1,3-dioxane
A
4,4-dimethyl-1,3-dioxane
B
3-methyl-butane-1,3-diol
Conditions | Yield |
---|---|
With formaldehyd; sulfuric acid In hexane at 70℃; Product distribution; var. time; |
Conditions | Yield |
---|---|
With sulfuric acid at 25℃; Rate constant; Mechanism; | |
Multi-step reaction with 2 steps 1: HCl 2: NaOH / 150 °C View Scheme |
2-methyl-3-buten-2-ol
A
2-methyl-1-buten-4-ol
B
formaldehyd
C
3-methyl-butane-1,3-diol
D
3-methyl-2-buten-1-ol
E
tert-butyl alcohol
Conditions | Yield |
---|---|
With sulfuric acid at 25℃; Product distribution; Rate constant; acid-catalyzed isomerization, dehydratation and decomposition of isopentenols, retro-Prince reaction; |
2-methyl-3-buten-2-ol
A
2-methyl-1-buten-4-ol
B
formaldehyd
C
3-methyl-butane-1,3-diol
D
3-methyl-2-buten-1-ol
E
isobutene
F
isoprene
Conditions | Yield |
---|---|
With sulfuric acid In water at 25℃; Kinetics; Mechanism; |
acetaldehyde
isobutene
A
4,4-dimethyl-1,3-dioxane
B
2,4,4,6-tetramethyl-1,3-dioxane
C
3-methyl-butane-1,3-diol
D
2,4,4-trimethyl-1,3-dioxane
Conditions | Yield |
---|---|
sulfuric acid In various solvent(s) at 70℃; for 5.33333h; steel bomb; Further byproducts given. Title compound not separated from byproducts; | A 6.1 mmol B 7.5 mmol C n/a D 16.4 mmol |
sulfuric acid In various solvent(s) at 70℃; for 4.33333h; steel bomb; Further byproducts given. Title compound not separated from byproducts; | A 5.6 mmol B 8.5 mmol C n/a D 16.4 mmol |
sulfuric acid In various solvent(s) at 70℃; for 3h; steel bomb; Further byproducts given. Title compound not separated from byproducts; | A 4.8 mmol B 4.9 mmol C n/a D 21.6 mmol |
formaldehyd
sulfuric acid
isobutene
A
4,4-dimethyl-1,3-dioxane
B
4,4-dimethyl-5-hydroxymethyl-1,3-dioxane
C
3-methyl-butane-1,3-diol
D
2-hydroxymethyl-3-methyl-butane-1,3-diol
Conditions | Yield |
---|---|
at 85 - 115℃; under 5884.06 - 10297.1 Torr; analoge Reaktion mit Acetaldehyd; |
Conditions | Yield |
---|---|
Stage #1: pent-4-enoic acid With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 0.5h; Stage #2: 3-methyl-butane-1,3-diol In dichloromethane at 20℃; | 100% |
3-methyl-butane-1,3-diol
Conditions | Yield |
---|---|
With tetra(n-butyl)ammonium hydroxide; sodium hydroxide In tetrahydrofuran; water; toluene at 3.6 - 20℃; for 9.5h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
Stage #1: 3-methyl-butane-1,3-diol With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: 5-bromo-2-fluoropyridine In N,N-dimethyl-formamide at 0 - 20℃; for 18h; Inert atmosphere; | 100% |
3-methyl-butane-1,3-diol
carbonic acid dimethyl ester
1,1-dimethyl-trimethylene carbonate
Conditions | Yield |
---|---|
Stage #1: 3-methyl-butane-1,3-diol; carbonic acid dimethyl ester With Novozym435 at 60℃; for 7h; Molecular sieve; Enzymatic reaction; Stage #2: at 90℃; for 65h; chemoselective reaction; | 99.3% |
In neat (no solvent) at 120℃; for 3h; Molecular sieve; Green chemistry; | 98.2% |
3-methyl-butane-1,3-diol
di-tert-butyl dicarbonate
Conditions | Yield |
---|---|
With zinc diacetate In dichloromethane for 12.33h; Heating; | 98% |
3-methyl-butane-1,3-diol
methacrylic acid methyl ester
A
3-methyl-3-hydroxy-1-butyl methacrylate
Conditions | Yield |
---|---|
With 1,1,1-trioctyl-1-methylphosphonium methylcarbonate; 4,4'-di-tert-butylbiphenyl at 50℃; for 2h; Temperature; Schlenk technique; Molecular sieve; | A 98% B 2% |
With 1,1,1-trioctyl-1-methylphosphonium methylcarbonate at 20℃; for 3h; Molecular sieve; Green chemistry; chemoselective reaction; | A 97% B 3% |
With tetramethylammonium methyl carbonate at 80℃; for 6h; Molecular sieve; Green chemistry; chemoselective reaction; | A 3% B 97% |
Conditions | Yield |
---|---|
With antimonypentachloride In dichloromethane at 0℃; for 0.25h; | 97% |
3-methyl-butane-1,3-diol
p-toluenesulfonyl chloride
3-hydroxy-3-methylbutyl toluene-4-sulfonate
Conditions | Yield |
---|---|
With pyridine at 0℃; for 2h; | 97% |
With pyridine at 20℃; for 8h; | 90% |
With pyridine at 0 - 20℃; for 16h; | 90% |
3-methyl-butane-1,3-diol
acetyl chloride
3-hydroxy-3-methylbutyl acetate
Conditions | Yield |
---|---|
With calcium oxide In 2-methyltetrahydrofuran at 20℃; for 6h; Green chemistry; chemoselective reaction; | 96% |
With pyridine In diethyl ether 1) -15 deg C, 2) room temperature; |
3-methyl-butane-1,3-diol
tert-butylchlorodiphenylsilane
4-((tert-butyldiphenylsilyl)oxy)-2-methylbutan-2-ol
Conditions | Yield |
---|---|
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; Inert atmosphere; | 95% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 48h; | 78% |
With 1H-imidazole In dichloromethane |
3-methyl-butane-1,3-diol
benzoyl chloride
(3-hydroxy-3-methylbutyl) benzoate
Conditions | Yield |
---|---|
With iron(III)-acetylacetonate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 6h; Green chemistry; regioselective reaction; | 94% |
With iron(III)-acetylacetonate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 12h; | 75% |
With potassium carbonate In benzene Heating; |
3-methyl-butane-1,3-diol
malondialdehyde bis(diethyl acetal)
bis(4,4-dimethyl-1,3-dioxan-2-yl)methane
Conditions | Yield |
---|---|
With KU-2-8 cation-exchange resin In benzene at 120 - 130℃; heating until alcohol liberation was complete; | 93% |
Conditions | Yield |
---|---|
With C80H73NO6P2 In toluene at 20℃; for 48h; Molecular sieve; enantioselective reaction; | 93% |
3-methyl-butane-1,3-diol
p-toluenesulfonyl chloride
4-iodo-2-methylbutan-2-ol
Conditions | Yield |
---|---|
Stage #1: 3-methyl-butane-1,3-diol; p-toluenesulfonyl chloride With pyridine In dichloromethane at 0 - 20℃; for 16h; Stage #2: With sodium iodide In acetone for 2h; Finkelstein Reaction; | 93% |
3-methyl-butane-1,3-diol
triisopropylsilyl chloride
3-hydroxy-3-methylbutoxytriisopropylsilane
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide Inert atmosphere; | 91% |
Conditions | Yield |
---|---|
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; | 91% |
3-methyl-butane-1,3-diol
N-[(2Z)-3-butyl[1,3]thiazolo[4,5-c]pyridin-2(3H)-ylidene]-2-fluoro-5-(trifluoromethyl)benzamide
N-[(2Z)-3-butyl[1,3]thiazolo[4,5-c]pyridin-2(3H)-ylidene]-2-(3-hydroxy-3-methylbutoxy)-5-(trifluoromethyl)benzamide
Conditions | Yield |
---|---|
Stage #1: 3-methyl-butane-1,3-diol With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.333333h; Stage #2: N-[(2Z)-3-butyl[1,3]thiazolo[4,5-c]pyridin-2(3H)-ylidene]-2-fluoro-5-(trifluoromethyl)benzamide In tetrahydrofuran; mineral oil at 0 - 5℃; for 0.333333h; | 90% |
Stage #1: 3-methyl-butane-1,3-diol With sodium t-butanolate In tetrahydrofuran at 0 - 5℃; for 0.5h; Stage #2: N-[(2Z)-3-butyl[1,3]thiazolo[4,5-c]pyridin-2(3H)-ylidene]-2-fluoro-5-(trifluoromethyl)benzamide In tetrahydrofuran at 0℃; for 4h; | 72% |
3-methyl-butane-1,3-diol
1-benzoylimidazole
(3-hydroxy-3-methylbutyl) benzoate
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 50℃; for 8h; regioselective reaction; | 90% |
Conditions | Yield |
---|---|
With 10H-phenothiazine at 120℃; for 9h; Reagent/catalyst; | 90% |
With 10H-phenothiazine; N,N'-bis(salicylidene)ethylenediamine iron(II) at 100 - 105℃; for 11h; Molecular sieve; | |
With 10H-phenothiazine; (μ-oxo)bis[(1,2-ethanediamino-N,N'-bis(salicylidene))iron(III)] at 100 - 120℃; under 760.051 Torr; for 11h; Reagent/catalyst; Molecular sieve; | 99.99 %Chromat. |
3-methyl-butane-1,3-diol
Conditions | Yield |
---|---|
Stage #1: 3-methyl-butane-1,3-diol With potassium hexamethylsilazane In tetrahydrofuran; N,N-dimethyl-formamide at 25℃; for 0.166667h; Inert atmosphere; Schlenk technique; Stage #2: 4-cyano-N,N,N-trimethylanilinium trifluoromethansulfonate In tetrahydrofuran; N,N-dimethyl-formamide at 25℃; for 3h; Inert atmosphere; Schlenk technique; | 90% |
3-methyl-butane-1,3-diol
methacrylic acid methyl ester
3-methyl-3-hydroxy-1-butyl methacrylate
Conditions | Yield |
---|---|
With TEMPOL; magnesium ethylate at 100 - 130℃; for 16h; | 89.3% |
With 4,4'-di-tert-butylbiphenyl; toluene-4-sulfonic acid at 80℃; for 3h; Temperature; Schlenk technique; Molecular sieve; | 3% |
With 10H-phenothiazine; Tridecane; N,N'-bis(salicylidene)ethylenediamine iron(II) at 100 - 120℃; for 1h; |
Conditions | Yield |
---|---|
With sodium azide; (Dichloroiodo)benzene In ethyl acetate at 0 - 80℃; for 12h; Concentration; Curtius Rearrangement; Inert atmosphere; | 89% |
3-methyl-butane-1,3-diol
benzyl bromide
1-O-benzyl-3-methyl-1,3-butanediol
Conditions | Yield |
---|---|
With tris(2,6-dimethylheptane-3,5-dionato)iron(III); potassium carbonate In acetonitrile at 80℃; for 24h; regioselective reaction; | 88% |
With sodium hydride In mineral oil |
3-methyl-butane-1,3-diol
Conditions | Yield |
---|---|
Stage #1: 4-(α-bromo-isobutyrylamino)-benzoic acid With dmap; triethylamine; 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 3h; Inert atmosphere; Stage #2: 3-methyl-butane-1,3-diol In dichloromethane at 20℃; for 14h; Inert atmosphere; | 88% |
Stage #1: 4-(α-bromo-isobutyrylamino)-benzoic acid With dmap; triethylamine; 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 3h; Stage #2: 3-methyl-butane-1,3-diol In dichloromethane at 20℃; for 14h; | 65% |
3-methyl-butane-1,3-diol
allyl bromide
4-(allyloxy)-2-methylbutan-2-ol
Conditions | Yield |
---|---|
With potassium hydroxide In tetrahydrofuran at 70℃; for 16.5h; | 88% |
3-methyl-butane-1,3-diol
carbonic acid dimethyl ester
A
1,1-dimethyl-trimethylene carbonate
B
C7H14O4
Conditions | Yield |
---|---|
at 80 - 120℃; for 72h; Product distribution / selectivity; | A 86.3% B 11.6% |
3-methyl-butane-1,3-diol
bis(diethylamino)dimethylsilane
2,2,4,4-tetramethyl-1,3-dioxa-2-silacyclo-hexane
Conditions | Yield |
---|---|
In 1,4-dioxane Heating; | 86% |
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