Introduction 2,2,4-Trimethyl-1,3-pentanediol TMPD CAS (144-19-4) is a kind of white crystal, can soluble in alcohol, ketone, aromatic hydrocarbon solvents, soluble in water and fat hydrocarbon. It mainly used in the manufacture of polyester resin,
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inquirySpecifications 2 2 4 - trimethyl-1 3-pentanediol/144-19-4 Molecular Formula C8H18O2 Molecular Weight 146.23 CAS Registry Number 144-19-4 2,2,4 - trimethyl-1,3-pentanediol/144-19-4 Application: 2,2,4-Trimethylpentane
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inquirytexanol
A
2,2,4-trimethylpentan-1,3-diol
B
2,2,4-trimethyl-1,3-pentanediol diisobutyrate
Conditions | Yield |
---|---|
With Cr2O3/SO42 solid acid catalyst at 160℃; for 6h; Reagent/catalyst; Temperature; | A n/a B 93% |
Conditions | Yield |
---|---|
With nickel In sodium hydroxide at 20℃; Electrochemical reaction; | 92% |
With sodium hydroxide | |
With calcium hydroxide |
ethene
isobutyraldehyde
B
2,2,4-trimethylpentan-1,3-diol
C
(2R,3S)-2,4-dimethyl-1,3-pentane diol
Conditions | Yield |
---|---|
Stage #1: ethene; isobutyraldehyde With carbon monoxide; hydrogen; triphenylphosphine; acetylacetonatodicarbonylrhodium(l); L-proline In N,N-dimethyl-formamide at 5℃; under 22502.3 Torr; for 48h; Stage #2: With sodium tetrahydroborate In methanol; N,N-dimethyl-formamide at 0℃; for 0.666667h; Further stages.; | A n/a B n/a C 76% |
7-Isopropyl-8,8-dimethyl-8,9-dihydro-7H-6,10-dioxabenzocyclononene-5,11-dione
2,2,4-trimethylpentan-1,3-diol
Conditions | Yield |
---|---|
48% |
5,5-dimethyl-2,6-bis(propan-2-yl)-1,3-dioxan-4-ol
2,2,4-trimethylpentan-1,3-diol
Conditions | Yield |
---|---|
With water; nickel at 50 - 85℃; Hydrogenation; | |
With hydrogen; chromium nickel | |
Multi-step reaction with 2 steps 1: aqueous acetic acid / Abdestillieren des entstehenden Isobutyraldehyds 2: Raney nickel; water / 125 - 165 °C / Hydrogenation View Scheme |
Conditions | Yield |
---|---|
With sodium amalgam; ethanol; sulfuric acid | |
With water; nickel at 125 - 165℃; Hydrogenation; |
3-hydroxy-2,2,4-trimethyl-pentanal
A
2,2,4-trimethylpentan-1,3-diol
B
isobutyric Acid
Conditions | Yield |
---|---|
With potassium hydroxide zuletzt bei Siedetemperatur; |
isobutyraldehyde
A
2,2,4-trimethylpentan-1,3-diol
B
3-hydroxy-2,2,4-trimethyl-pentanal
Conditions | Yield |
---|---|
With potassium hydroxide |
Conditions | Yield |
---|---|
With sodium hydroxide at 200℃; | |
With water; calcium carbonate at 150℃; under 40452.9 Torr; |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride |
Conditions | Yield |
---|---|
With sodium hydroxide In methanol |
isobutyraldehyde
acetylene
A
2,2,4-trimethylpentan-1,3-diol
B
4-methylpent-1-yn-3-ol
C
3-hydroxy-2,2,4-trimethyl-pentanal
Conditions | Yield |
---|---|
at 20 - 25℃; |
diethyl ether
isobutyraldehyde
acetylene
A
2,2,4-trimethylpentan-1,3-diol
B
4-methylpent-1-yn-3-ol
C
3-hydroxy-2,2,4-trimethyl-pentanal
Conditions | Yield |
---|---|
at 20 - 25℃; |
2,2,4-trimethylpentan-1,3-diol
Conditions | Yield |
---|---|
durch Verseifen; | |
With alkaline solution |
ethanol
3-hydroxy-2,2,4-trimethyl-pentanal
sulfuric acid
2,2,4-trimethylpentan-1,3-diol
2,2,4-trimethyl-3-hydroxyvaleric acid
A
2,2,4-trimethylpentan-1,3-diol
B
isobutyric Acid
3-hydroxy-2,2,4-trimethyl-pentanal
A
2,2,4-trimethylpentan-1,3-diol
B
isobutyric Acid
Conditions | Yield |
---|---|
at 25℃; |
3-(α-hydroxy-isobutoxy)-2,2,4-trimethyl-valeraldehyde
A
2,2,4-trimethylpentan-1,3-diol
B
isobutyric Acid
2,4-dihydroxy-3,3,5-trimethyl-hexanenitrile
A
2,2,4-trimethylpentan-1,3-diol
B
hydrogen cyanide
C
isobutyric Acid
2,2,4,4-tetramethyl-1,3-cyclobutanedione
A
2,2,4-trimethylpentan-1,3-diol
B
2,2,4-trimethyl-3-oxo-1-pentanol
E
3-hydroxy-2,2,4,4-tetramethylcyclobutane-1-one
Conditions | Yield |
---|---|
With hydrogen; A280 cobalt on alumina catalyst In isobutyl isobutanoate at 165℃; under 25877.6 - 75007.5 Torr; for 2h; Product distribution / selectivity; | |
With hydrogen; A280 cobalt on alumina catalyst promoted with Ir(OAc)x In isobutyl isobutanoate at 135 - 165℃; under 25877.6 - 75007.5 Torr; for 2h; Product distribution / selectivity; | |
With hydrogen; G-96B-RS 62percent nickel on kieselguhr catalyst In isobutyl isobutanoate at 160℃; under 46504.7 Torr; for 3h; Product distribution / selectivity; |
2,2,4,4-tetramethyl-1,3-cyclobutanedione
A
2,2,4-trimethylpentan-1,3-diol
D
3-hydroxy-2,2,4,4-tetramethylcyclobutane-1-one
Conditions | Yield |
---|---|
With hydrogen; G-67A 20percent cobalt on silica catalyst In isobutyl isobutanoate at 135℃; under 25877.6 Torr; for 2h; Product distribution / selectivity; | |
With hydrogen; cesium-promoted copper on silica catalyst In isobutyl isobutanoate at 135℃; under 75007.5 Torr; for 2h; Product distribution / selectivity; |
2,2,4,4-tetramethyl-1,3-cyclobutanedione
A
2,2,4-trimethylpentan-1,3-diol
B
2,2,4-trimethyl-3-oxo-1-pentanol
Conditions | Yield |
---|---|
With hydrogen; chromium-promoted KL2015-T5 copper on zinc oxide catalyst In isobutyl isobutanoate at 135℃; under 25877.6 - 75007.5 Torr; for 2h; Product distribution / selectivity; |
Conditions | Yield |
---|---|
With hydrogen; cesium-promoted copper on silica catalyst In isobutyl isobutanoate at 165℃; under 25877.6 - 75007.5 Torr; for 2h; Product distribution / selectivity; | |
With hydrogen; chromium-promoted KL2015-T5 copper on zinc oxide catalyst In isobutyl isobutanoate at 135 - 165℃; under 75007.5 Torr; for 2h; Product distribution / selectivity; |
A
2,2,4-trimethyl-1-pentanol
B
2,2,4-trimethylpentan-1,3-diol
C
2,2,4-trimethyl-3-pentanol
D
2,4-dimethyl-3-pentanol
Conditions | Yield |
---|---|
With isobutyl isobutanoate; 5 % platinum on carbon at 50 - 200℃; under 5250.53 - 21002.1 Torr; Product distribution / selectivity; Inert atmosphere; |
isobutyraldehyde
A
2,2,4-trimethylpentan-1,3-diol
B
texanol
C
2,2,4-trimethyl-1,3-pentanediol diisobutyrate
D
2-methylpropionic acid 3-hydroxy-2,2-dimethyl-1-(1-methylethyl)propyl ester
E
isobutyric Acid
Conditions | Yield |
---|---|
With sodium hydroxide In water at 60℃; for 4h; Concentration; Overall yield = 63.6 %Chromat.; |
isobutyraldehyde
A
2,2,4-trimethylpentan-1,3-diol
B
3-hydroxy-2,2,4-trimethyl-pentanal
C
texanol
D
2-methylpropionic acid 3-hydroxy-2,2-dimethyl-1-(1-methylethyl)propyl ester
E
isobutyric Acid
Conditions | Yield |
---|---|
Stage #1: isobutyraldehyde With sodium hydroxide at 60℃; for 4h; Stage #2: With hydrogenchloride Concentration; Overall yield = 59.3 %Chromat.; |
isobutyraldehyde
A
2,2,4-trimethylpentan-1,3-diol
B
texanol
C
2-methylpropionic acid 3-hydroxy-2,2-dimethyl-1-(1-methylethyl)propyl ester
D
isobutyric Acid
Conditions | Yield |
---|---|
Stage #1: isobutyraldehyde With sodium hydroxide at 60℃; for 4h; Stage #2: With hydrogenchloride Concentration; Overall yield = 85.4 %Chromat.; |
2,2,4-trimethylpentan-1,3-diol
2,2,4-trimethyl-3-oxo-1-pentanol
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; [π-C5H5N(+)(CH2)15CH3]3(PMo12O40)(3-) In benzene for 24h; Heating; | 100% |
With dihydrogen peroxide In water; tert-butyl alcohol at 80℃; for 12h; chemoselective reaction; | 99% |
With iron(III) chloride; 1,1,1,3',3',3'-hexafluoro-propanol; oxygen; nitric acid at 20℃; for 5h; Catalytic behavior; | 96% |
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 0℃; for 2h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With 1-methyl-1H-imidazole; tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate; 4,4'-Dimethoxy-2,2'-bipyridin; 9-azabicyclo[3.3.1]nonane N-oxyl; oxygen In acetonitrile at 20℃; for 0.5h; | 98% |
With 1‐methyl‐2‐azaadamantane‐N‐oxyl; sodium hypochlorite; tetrabutylammomium bromide; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at 0℃; for 0.333333h; | 96% |
With sodium hypochlorite; 1,5-dimethyl-9-azanoradamantane N-oxyl; tetrabutylammomium bromide; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at 0℃; for 0.333333h; Reagent/catalyst; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene at 105℃; for 7h; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With potassium dihydrogenphosphate; sodium hydrogensulfate monohydrate at 160℃; for 8h; Reagent/catalyst; Inert atmosphere; | 97% |
2,2,4-trimethylpentan-1,3-diol
chlorodimethyl(1,1,2-trimethylpropyl)silane
dimethyl(3-hydroxy-2,2,4-trimethylpentyloxy)(1,1,2-trimethylpropyl)silane
Conditions | Yield |
---|---|
With 1-methyl-1H-imidazole; iodine In dichloromethane at 20℃; for 0.0833333h; | 96% |
2,2,4-trimethylpentan-1,3-diol
3-Chloro-2-methylpropene
1-(2-methyl-2-propenyloxy)-2,2,4-trimethylpentan-3-ol
Conditions | Yield |
---|---|
Stage #1: 2,2,4-trimethylpentan-1,3-diol With sodium hydroxide; tetrabutylammomium bromide In water at 50℃; Stage #2: 3-Chloro-2-methylpropene In water at 100℃; for 3.83333h; | 94.1% |
2,2,4-trimethylpentan-1,3-diol
(1S,2R)-1,2-diphenylethane-1,2-diol
4-isopropyl-5,5-dimethyl-2-phenyl-1,3-dioxane
Conditions | Yield |
---|---|
With PTAB; N-benzyl-N,N,N-triethylammonium chloride; antimony(III) bromide In dimethyl sulfoxide at 20℃; for 61h; | 94% |
2,2,4-trimethylpentan-1,3-diol
allyl bromide
1,3-bis(allyloxy)-2,2,4-trimethylpentane
Conditions | Yield |
---|---|
Stage #1: 2,2,4-trimethylpentan-1,3-diol With sodium hydride In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere; Stage #2: allyl bromide In tetrahydrofuran at 20℃; Inert atmosphere; Reflux; | 93% |
2,2,4-trimethylpentan-1,3-diol
2,2,4-trimethyl-3-hydroxyvaleric acid
Conditions | Yield |
---|---|
With sodium hypochlorite; sodium chlorite; 1,5-dimethyl-9-azanoradamantane N-oxyl In aq. phosphate buffer; acetonitrile at 25℃; for 7h; pH=6.8; Catalytic behavior; Reagent/catalyst; | 92% |
With potassium permanganate; water |
2,2,4-trimethylpentan-1,3-diol
A
3-hydroxy-2,2,4-trimethyl-pentanal
B
3-oxo-2,2,4-trimetheyl-1-pentanal
Conditions | Yield |
---|---|
With sodium hypochlorite; C9H14NO; tetrabutylammomium bromide; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at 0℃; for 0.333333h; Inert atmosphere; | A 92% B 6% |
With sodium hypochlorite; 1,5-dimethyl-9-azanoradamantane N-oxyl; tetrabutylammomium bromide; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at 0℃; for 0.333333h; | A 69% B 17% |
diazomethane
2,2,4-trimethylpentan-1,3-diol
methyl 3-hydroxy-2,2,4-trimethylpentanoate
Conditions | Yield |
---|---|
Stage #1: 2,2,4-trimethylpentan-1,3-diol With sodium hypochlorite; sodium chlorite; 1,5-dimethyl-9-azanoradamantane N-oxyl In aq. phosphate buffer; water; acetonitrile for 7h; pH=6.8; Inert atmosphere; Stage #2: diazomethane In diethyl ether Reagent/catalyst; Inert atmosphere; | 92% |
2,2,4-trimethylpentan-1,3-diol
trans-Stilbene oxide
4-isopropyl-5,5-dimethyl-2-phenyl-1,3-dioxane
Conditions | Yield |
---|---|
With PTAB; N-benzyl-N,N,N-triethylammonium chloride; antimony(III) bromide In dimethyl sulfoxide at 20℃; for 46h; | 91% |
2,2,4-trimethylpentan-1,3-diol
benzoic acid
2,2,4-Trimethyl-1,3-pentanediol Dibenzoate
Conditions | Yield |
---|---|
With H2SO4/TiO2-La2O3-solid acid catalyst In dibutyl ether at 170 - 180℃; for 10h; | 90.5% |
tert-butyl acetoacetate
2,2,4-trimethylpentan-1,3-diol
2,2,4-Trimethylpentane-1,3-diol bisacetoacetate
Conditions | Yield |
---|---|
In xylene for 0.5h; Heating; | 87% |
2,2,4-trimethylpentan-1,3-diol
acetic anhydride
1,3-diacetoxy-2,2,4-trimethyl-pentane
Conditions | Yield |
---|---|
bismuth(lll) trifluoromethanesulfonate In acetonitrile at 20℃; for 1h; | 87% |
Conditions | Yield |
---|---|
With sodium hypochlorite; 1-methyl-2-azaadamantane-N-oxyl; tetrabutylammomium bromide; potassium bromide In dichloromethane; sodium hydrogencarbonate at 0℃; for 0.333333h; | 87% |
With 1‐methyl‐2‐azaadamantane‐N‐oxyl; sodium hypochlorite; tetrabutylammomium bromide; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at 0℃; for 0.333333h; | 87% |
With sodium hypochlorite; 3-methyl-4-oxa-5-azahomoadamantane; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at 0℃; for 0.333333h; Inert atmosphere; | 84% |
With polystyrene-supported oxorhenium catalyst activated by iPrOH; dimethyl sulfoxide In toluene for 15h; Heating; Dean-Stark apparatus; | 82% |
With sodium hypochlorite; C8H12NO; tetrabutylammomium bromide; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at 0℃; for 0.333333h; Inert atmosphere; | 72% |
2,2,4-trimethylpentan-1,3-diol
3-hydroxy-2,2,4-trimethylpentanenitrile
Conditions | Yield |
---|---|
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; ammonium acetate In water; acetonitrile at 20℃; for 8h; chemoselective reaction; | 87% |
2,2,4-trimethylpentan-1,3-diol
1,1,2-triphenyl-1,2-ethanediol
A
benzophenone
B
4-isopropyl-5,5-dimethyl-2-phenyl-1,3-dioxane
Conditions | Yield |
---|---|
With PTAB; N-benzyl-N,N,N-triethylammonium chloride; antimony(III) bromide In dimethyl sulfoxide at 20℃; for 42h; | A 86% B 84% |
2,2,4-trimethylpentan-1,3-diol
diphenylsilanediol
boric acid
(C6H5)2Si(OBO2C3H3(CH3)2CH(CH3)2)2
Conditions | Yield |
---|---|
In toluene byproducts: H2O; inert atmosphere; refluxing (8 h); evapn., hexanes addn., filtering, pptn. on concg. (-22°C, severalh); elem. anal.; | 85.2% |
2,2,4-trimethylpentan-1,3-diol
isobutyryl chloride
2,2,4-trimethyl-1,3-pentanediol diisobutyrate
Conditions | Yield |
---|---|
With zinc(II) chloride In dichloromethane at 0 - 40℃; Molecular sieve; | 85.2% |
2,2,4-trimethylpentan-1,3-diol
2-(4-bromomethyl-2-methoxyphenyl)benzothiazole
1-[4-(benzothiazol-2-yl)-3-methoxybenzyloxyl]-2,2,4-trimethylpentan-3-ol
Conditions | Yield |
---|---|
Stage #1: 2,2,4-trimethylpentan-1,3-diol With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.666667h; Inert atmosphere; Stage #2: 2-(4-bromomethyl-2-methoxyphenyl)benzothiazole In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 20℃; for 2h; Williamson synthesis; Inert atmosphere; | 85% |
2,2,4-trimethylpentan-1,3-diol
carbonic acid dimethyl ester
A
methanol
B
4-isopropyl-5,5-dimethyl-[1,3]dioxan-2-one
Conditions | Yield |
---|---|
zinc(II) acetylacetonate at 20 - 155℃; for 10.5h; Product distribution / selectivity; Neat (no solvent); Reflux/azeotropic distillation; | A n/a B 84.9% |
zinc diacetate at 20 - 155℃; for 12.5h; Product distribution / selectivity; Neat (no solvent); Reflux/azeotropic distillation; | A n/a B 81.3% |
tin(II) octanoate at 20 - 155℃; for 18h; Product distribution / selectivity; Neat (no solvent); Reflux/azeotropic distillation; | A n/a B 78.2% |
zinc stearate at 20 - 155℃; for 18h; Product distribution / selectivity; Neat (no solvent); Reflux/azeotropic distillation; | A n/a B 73.5% |
2,2,4-trimethylpentan-1,3-diol
A
3-hydroxy-2,2,4-trimethyl-pentanal
B
2,2,4-trimethyl-3-hydroxyvaleric acid
Conditions | Yield |
---|---|
With sodium hypochlorite; 1,5-dimethyl-9-azanoradamantane N-oxyl; tetrabutylammomium bromide; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at 0℃; for 0.333333h; Reagent/catalyst; Inert atmosphere; | A 81% B 6% |
2,2,4-trimethylpentan-1,3-diol
1,1,3,3-tetraphenyldisiloxane-1,3-diol
boric acid
O(Si(C6H5)2OBO2C3H3(CH3)2CH(CH3)2)2
Conditions | Yield |
---|---|
In not given byproducts: H2O; inert atmosphere; elem. anal.; | 80% |
2,2,4-trimethylpentan-1,3-diol
trans-2-chloro-4-isopropyl-5,5-dimethyl-1,3,2-dioxaphosphorinane
Conditions | Yield |
---|---|
With triethylamine; phosphorus trichloride In benzene for 4h; Ambient temperature; | 76% |
With triethylamine; phosphorus trichloride In diethyl ether for 2h; Ambient temperature; | 71% |
2,2,4-trimethylpentan-1,3-diol
Conditions | Yield |
---|---|
With silica gel; sodium hydroxide for 24h; Reagent/catalyst; Inert atmosphere; | 73% |
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