trans-1,4-cyclohexylenedimethylene diacetate
trans-1,4-Cyclohexanedimethanol
Conditions | Yield |
---|---|
With potassium carbonate Ambient temperature; | 100% |
With sodium hydroxide for 10h; Heating; | 46.3% |
Conditions | Yield |
---|---|
With zinc borohydride pyridine complex In tetrahydrofuran for 0.4h; Heating; | 96% |
Stage #1: trans-hexahydroterephthalic acid With thionyl chloride In methanol at 0℃; for 4h; Reflux; Stage #2: With sodium tetrahydroborate In tetrahydrofuran for 0.5h; Reflux; Stage #3: With methanol In tetrahydrofuran for 12h; Reflux; | 28.6% |
(±)-trans-[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclohexyl]methanol
trans-1,4-Cyclohexanedimethanol
Conditions | Yield |
---|---|
With sodium tetrachloroaurate(III) dihydrate In methanol at 20℃; for 2h; | 96% |
Conditions | Yield |
---|---|
With water; sodium hydroxide In methanol at 70℃; | 88.55% |
diethyl cyclohexane-trans-1,4-dicarboxylate
trans-1,4-Cyclohexanedimethanol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In diethyl ether at 20℃; Reduction; | 77% |
Conditions | Yield |
---|---|
With Ni/NiO-diatomite at 200℃; for 3h; Reagent/catalyst; Autoclave; Inert atmosphere; | 72.6% |
Multi-step reaction with 2 steps 1: 52.1 percent / 140 - 165 °C 2: 46.3 percent / aq. NaOH / 10 h / Heating View Scheme |
Conditions | Yield |
---|---|
In acetone for 168h; Ambient temperature; lipase PS (Pseudomonas sp.) on Celite; Yields of byproduct given; | A 66% B n/a C n/a |
dimethyl 1,4-cyclohexanedicarboxylate
A
trans-1,4-Cyclohexanedimethanol
B
(1s,4s)-cyclohexane-1,4-diyldimethanol
Conditions | Yield |
---|---|
With methanol; sodium Trennung ueber die Dibenzoyl-Derivate; |
cis-dimethyl 1,4-cyclohexanedicarboxylate
A
trans-1,4-Cyclohexanedimethanol
B
(1s,4s)-cyclohexane-1,4-diyldimethanol
Conditions | Yield |
---|---|
With methanol; sodium Trennung ueber die Dibenzoyl-Derivate; |
trans-1,4-bis-methanesulfonyloxymethyl-cyclohexane
A
4-methylene-1-cyclohexanemethanol
B
trans-1,4-Cyclohexanedimethanol
Conditions | Yield |
---|---|
With potassium hydroxide |
A
trans-1,4-Cyclohexanedimethanol
Conditions | Yield |
---|---|
With dichloro-acetic acid; water In 1,4-dioxane-d8 at 37℃; Kinetics; Hydrolysis; |
1,4-benzenedicarboxylic acid dimethyl ester
A
trans-1,4-Cyclohexanedimethanol
B
(1s,4s)-cyclohexane-1,4-diyldimethanol
Conditions | Yield |
---|---|
With hydrogen; aluminum oxyhydroxide; rhodium In ethyl acetate at 22℃; under 760 Torr; for 46h; Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
In tetrahydrofuran; (2S)-N-methyl-1-phenylpropan-2-amine hydrate | |
With copper chromium; hydrogen at 210℃; under 152940 Torr; |
terephthalic acid
A
trans-1,4-Cyclohexanedimethanol
B
(1s,4s)-cyclohexane-1,4-diyldimethanol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 6 h / 260 - 280 °C / 4535.33 Torr 2: dimethyl 1,4-cyclohexane dicarboxylate; Pd/Al2O3; hydrogen / 1 h / 200 °C / 93849.2 Torr / Autoclave 3: C16H30O; (4-methylcyclohexyl)methanol / 225 °C / 258581 Torr View Scheme | |
Multi-step reaction with 3 steps 1: 4 h / 280 °C / 4535.33 Torr / Large scale 2: ; hydrogen / 1 h / 200 °C / 93849.2 Torr / Autoclave 3: CrO4(2-)*Ba(2+)*Cr2CuO4*CuO; hydrogen / 5 h / 250 °C / 212036 Torr View Scheme | |
Multi-step reaction with 3 steps 1: 8.5 h / 260 - 280 °C / 4535.33 Torr / Large scale 2: Pd/Al2O3; hydrogen; dimethyl 1,4-cyclohexane dicarboxylate / 1 h / 200 °C / 93849.2 Torr / Autoclave 3: Pd/Al2O3; C16H30O; (4-methylcyclohexyl)methanol / 225 °C / 259341 Torr View Scheme | |
Multi-step reaction with 3 steps 1: 8.5 h / 260 - 280 °C / 4535.33 Torr / Large scale 2: Pd/Al2O3; hydrogen; (4-methylcyclohexyl)methanol / 180 - 225 °C / 93849.2 Torr 3: Pd/Al2O3; C16H30O; (4-methylcyclohexyl)methanol / 225 °C / 259341 Torr View Scheme |
bis((4-methylcyclohexyl)methyl) cyclohexane-1,4-dicarboxylate
A
trans-1,4-Cyclohexanedimethanol
B
(1s,4s)-cyclohexane-1,4-diyldimethanol
C
(4-methylcyclohexyl)methanol
Conditions | Yield |
---|---|
With CrO4(2-)*Ba(2+)*Cr2CuO4*CuO; hydrogen at 250℃; under 212036 Torr; for 5h; Pressure; Temperature; |
terephthalic acid 1,4-bis(4-methylcyclohexyl)methyl ester
A
trans-1,4-Cyclohexanedimethanol
B
(1s,4s)-cyclohexane-1,4-diyldimethanol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Pd/Al2O3; hydrogen; dimethyl 1,4-cyclohexane dicarboxylate / 1 h / 200 °C / 93849.2 Torr / Autoclave 2: Pd/Al2O3; C16H30O; (4-methylcyclohexyl)methanol / 225 °C / 259341 Torr View Scheme |
bis((4-methylcyclohexyl)methyl) cyclohexane-1,4-dicarboxylate
A
trans-1,4-Cyclohexanedimethanol
B
(1s,4s)-cyclohexane-1,4-diyldimethanol
Conditions | Yield |
---|---|
With C16H30O; (4-methylcyclohexyl)methanol at 225℃; under 258581 Torr; | |
With (4-methylcyclohexyl)methanol; hydrogen at 250℃; under 212036 Torr; for 5h; | A n/a B n/a |
With Pd/Al2O3; C16H30O; (4-methylcyclohexyl)methanol at 225℃; under 259341 Torr; | A n/a B n/a |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at -20 - 20℃; for 3h; Large scale; |
trans-1,4-Cyclohexanedimethanol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium tetrachloroaurate(III) dihydrate / methanol / 1 h / 20 °C 2: sodium tetrachloroaurate(III) dihydrate / methanol / 2 h / 20 °C View Scheme |
trans-1,4-Cyclohexanedimethanol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 10 wt% Pd(OH)2 on carbon; hydrogen / methanol; ethyl acetate / 18 h / 3345.86 Torr 2: potassium carbonate; methanol / 17 h / 20 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 10 wt% Pd(OH)2 on carbon; hydrogen / methanol; ethyl acetate / 18 h / 3345.86 Torr 2: potassium carbonate / methanol / 17 h / 20 °C View Scheme |
(2E,4E)-hexa-2,4-diene-1,6-diol
trans-1,4-Cyclohexanedimethanol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: triethylamine; dmap / dichloromethane / 16 h 2: m-xylene / 1 h / 250 °C / 11103.3 - 78334.3 Torr / Autoclave; Inert atmosphere 3: 10 wt% Pd(OH)2 on carbon; hydrogen / methanol; ethyl acetate / 18 h / 3345.86 Torr 4: potassium carbonate; methanol / 17 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1: t-butyl catechol / m-xylene / 12 h / 200 - 1217 °C / 11103.3 - 62819.5 Torr / Autoclave; Inert atmosphere; Sealed tube 2: triethylamine; dmap / dichloromethane / 1.75 h / 20 °C 3: 10 wt% Pd(OH)2 on carbon; hydrogen / methanol; ethyl acetate / 18 h / 3345.86 Torr 4: potassium carbonate; methanol / 17 h / 20 °C View Scheme |
(2E,4E)-hexa-2,4-diene-1,6-diol
A
trans-1,4-Cyclohexanedimethanol
B
(1s,4s)-cyclohexane-1,4-diyldimethanol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: t-butyl catechol / m-xylene / 12 h / 200 - 1217 °C / 11103.3 - 62819.5 Torr / Autoclave; Inert atmosphere; Sealed tube 2: hydrogen / isopropyl alcohol / 20 h / 3345.86 Torr / Autoclave View Scheme | |
Multi-step reaction with 4 steps 1: triethylamine; dmap / dichloromethane / 16 h 2: m-xylene / 1 h / 250 °C / 11103.3 - 78334.3 Torr / Autoclave; Inert atmosphere 3: 10 wt% Pd(OH)2 on carbon; hydrogen / methanol; ethyl acetate / 18 h / 3345.86 Torr 4: potassium carbonate / methanol / 17 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1: t-butyl catechol / m-xylene / 12 h / 200 - 1217 °C / 11103.3 - 62819.5 Torr / Autoclave; Inert atmosphere; Sealed tube 2: triethylamine; dmap / dichloromethane / 1.75 h / 20 °C 3: 10 wt% Pd(OH)2 on carbon; hydrogen / methanol; ethyl acetate / 18 h / 3345.86 Torr 4: potassium carbonate / methanol / 17 h / 20 °C View Scheme |
trans-1,4-Cyclohexanedimethanol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: triethylamine; dmap / dichloromethane / 1.75 h / 20 °C 2: 10 wt% Pd(OH)2 on carbon; hydrogen / methanol; ethyl acetate / 18 h / 3345.86 Torr 3: potassium carbonate; methanol / 17 h / 20 °C View Scheme |
Conditions | Yield |
---|---|
With hydrogen In isopropyl alcohol under 3345.86 Torr; for 20h; Pressure; Reagent/catalyst; Solvent; Autoclave; stereoselective reaction; | A 15.1 %Chromat. B 78.6 %Chromat. |
Multi-step reaction with 3 steps 1: triethylamine; dmap / dichloromethane / 1.75 h / 20 °C 2: 10 wt% Pd(OH)2 on carbon; hydrogen / methanol; ethyl acetate / 18 h / 3345.86 Torr 3: potassium carbonate / methanol / 17 h / 20 °C View Scheme |
Conditions | Yield |
---|---|
With potassium carbonate In methanol at 20℃; for 17h; Overall yield = 1.02 g; | A 0.44 %Spectr. B 82.3 %Spectr. |
A
terephthalic acid
B
trans-1,4-Cyclohexanedimethanol
C
(1s,4s)-cyclohexane-1,4-diyldimethanol
Conditions | Yield |
---|---|
With methanol; potassium carbonate at 20℃; for 17h; | A 0.12 %Chromat. B 0.48 %Chromat. C 90.5 %Chromat. |
(2E,4E)-hexa-2,4-diene-1,6-diacetate
trans-1,4-Cyclohexanedimethanol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: m-xylene / 1 h / 250 °C / 11103.3 - 78334.3 Torr / Autoclave; Inert atmosphere 2: 10 wt% Pd(OH)2 on carbon; hydrogen / methanol; ethyl acetate / 18 h / 3345.86 Torr 3: potassium carbonate; methanol / 17 h / 20 °C View Scheme |
(2E,4E)-hexa-2,4-diene-1,6-diacetate
A
trans-1,4-Cyclohexanedimethanol
B
(1s,4s)-cyclohexane-1,4-diyldimethanol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: m-xylene / 1 h / 250 °C / 11103.3 - 78334.3 Torr / Autoclave; Inert atmosphere 2: 10 wt% Pd(OH)2 on carbon; hydrogen / methanol; ethyl acetate / 18 h / 3345.86 Torr 3: potassium carbonate / methanol / 17 h / 20 °C View Scheme |
trans-1,4-Cyclohexanedimethanol
trans-1,4-bis-iodomethyl-cyclohexane
Conditions | Yield |
---|---|
With 1H-imidazole; iodine; triphenylphosphine In toluene at 60℃; for 2h; | 92% |
4-(dimethylamino)-1-((3-fluorophenyl)(phenyl)carbamoyl)pyridinium chloride
trans-1,4-Cyclohexanedimethanol
((1r,4r)-4-(hydroxymethyl)cyclohexyl)methyl-3-fluorophenyl(phenyl)carbamate
Conditions | Yield |
---|---|
With pyridine In acetonitrile at 53℃; for 18h; Large scale; | 83% |
With dmap In acetonitrile at 53℃; for 18h; |
trans-1,4-Cyclohexanedimethanol
tert-butyldimethylsilyl chloride
(±)-trans-[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclohexyl]methanol
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 29h; | 82% |
With pyridine In dichloromethane at 0 - 20℃; for 21h; | 68% |
With dmap; triethylamine In N,N-dimethyl-formamide at 0 - 25℃; for 22h; | 66% |
Conditions | Yield |
---|---|
With N-Bromosuccinimide In dichloromethane at 4℃; for 6h; | 79% |
Isopropenyl acetate
trans-1,4-Cyclohexanedimethanol
A
trans-1,4-cyclohexylenedimethylene diacetate
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; sodium carbonate In toluene at 100℃; for 6h; Inert atmosphere; | A n/a B 75% C n/a |
trans-1,4-Cyclohexanedimethanol
trans-1,4-Bis(bromomethyl)cyclohexane
Conditions | Yield |
---|---|
With phosphorus tribromide In N,N-dimethyl-formamide; toluene at 100℃; for 1.5h; Cooling with ice; | 71.28% |
at 135 - 140℃; Einleiten von HBr; | |
With hydrogen bromide | |
With pyridine; phosphorus tribromide In chloroform | |
With phosphorus tribromide In benzene Title compound not separated from byproducts; |
methyl 6-methyl-4-(2H-tetrazol-5-yl)picolinate
trans-1,4-Cyclohexanedimethanol
Conditions | Yield |
---|---|
With di-tert-butyl-diazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 18h; | 67% |
trans-1,4-Cyclohexanedimethanol
trans-1,4-Bis-cyclohexane
Conditions | Yield |
---|---|
With tetrachloromethane; triphenylphosphine | 64% |
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; | 62% |
Conditions | Yield |
---|---|
With pyridine at 0℃; for 2h; Esterification; | 61% |
Conditions | Yield |
---|---|
Stage #1: trans-1,4-Cyclohexanedimethanol With sodium hydride In tetrahydrofuran at 0 - 20℃; for 1h; Stage #2: benzyl bromide With tetra-(n-butyl)ammonium iodide In tetrahydrofuran at 20 - 60℃; for 15h; | 60% |
Stage #1: trans-1,4-Cyclohexanedimethanol With 15-crown-5; sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1h; | 45% |
In tetrahydrofuran; ethyl acetate |
(4-chlorophenyl)(phenyl)carbamic chloride
trans-1,4-Cyclohexanedimethanol
((1r,4r)-4-(hydroxymethyl)cyclohexyl)methyl (4-chlorophenyl)(phenyl)carbamate
Conditions | Yield |
---|---|
With pyridine Reflux; Large scale; | 60% |
With pyridine Sealed tube; Reflux; | 57% |
With pyridine Reflux; |
Conditions | Yield |
---|---|
Stage #1: trans-1,4-Cyclohexanedimethanol; terephthaloyl chloride With triethylamine In tetrahydrofuran at 20℃; for 13h; Inert atmosphere; Stage #2: With water; triethylamine In tetrahydrofuran | 59.6% |
trans-1,4-Cyclohexanedimethanol
p-toluenesulfonyl chloride
trans-4-(hydroxymethyl)cyclohexylmethyl 4-methylbenzenesulfonate
Conditions | Yield |
---|---|
With pyridine In chloroform for 4h; | 55.1% |
With dmap; triethylamine In dichloromethane for 36h; Ambient temperature; | 47% |
With triethylamine In dichloromethane at -20 - 20℃; for 10h; |
Conditions | Yield |
---|---|
Stage #1: trans-1,4-Cyclohexanedimethanol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: acetyl chloride In tetrahydrofuran; mineral oil at 15℃; for 3h; Inert atmosphere; | 53% |
trans-1,4-Cyclohexanedimethanol
phenyl isocyanate
((1r,4r)-4-(hydroxymethyl)cyclohexyl)methyl phenylcarbamate
Conditions | Yield |
---|---|
In pyridine at 20℃; for 5h; | 51.5% |
With pyridine at 20℃; for 5h; |
trans-1,4-Cyclohexanedimethanol
trans-1,4-cyclohexanedicarboxylic acid dichloride
Conditions | Yield |
---|---|
Stage #1: trans-1,4-Cyclohexanedimethanol; trans-1,4-cyclohexanedicarboxylic acid dichloride With triethylamine In tetrahydrofuran Inert atmosphere; Stage #2: With water; triethylamine In tetrahydrofuran | 50.9% |
trans-1,4-Cyclohexanedimethanol
3-(1-piperazinyl)-1,2-benzisothiazole
methanesulfonyl chloride
Conditions | Yield |
---|---|
Stage #1: trans-1,4-Cyclohexanedimethanol; methanesulfonyl chloride With triethylamine In ethyl acetate at 0 - 20℃; for 3h; Stage #2: 3-(1-piperazinyl)-1,2-benzisothiazole With sodium carbonate; potassium iodide In acetonitrile for 22h; Reflux; | 44.1% |
trans-1,4-Cyclohexanedimethanol
methyl iodide
(4-Methoxymethyl-cyclohexyl)-methanol
Conditions | Yield |
---|---|
With potassium hydride | 44% |
bromoacetic acid tert-butyl ester
trans-1,4-Cyclohexanedimethanol
tert-butyl 2-(((1r,4r)-4-(hydroxymethyl)cyclohexyl)methoxy)acetate
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide; sodium hydroxide In water; benzene at 20℃; for 2h; | 44% |
With tetra-(n-butyl)ammonium iodide; sodium hydroxide In water; benzene at 20℃; for 2h; |
trans-1,4-Cyclohexanedimethanol
4-(bromomethyl)cyclohexylmethanol
Conditions | Yield |
---|---|
With bromine; triphenylphosphine In N,N-dimethyl-formamide | 41% |
N-(3-methoxybenzyl)-6-methyl-4-(2H-tetrazol-5-yl)picolinamide
trans-1,4-Cyclohexanedimethanol
N-(3-methoxybenzyl)-4-(2-(((trans)-4-(hydroxymethyl)cyclohexyl)methyl)-2H-tetrazol-5-yl)-6-methylpicolinamide
Conditions | Yield |
---|---|
With di-tert-butyl-diazodicarboxylate In tetrahydrofuran for 18h; regioselective reaction; | 37% |
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran for 16h; Heating; | A 30% B 32% |
IUPAC Name: [4-(Hydroxymethyl)cyclohexyl]methanol
Structure of Trans-1,4-Cyclohexanedimethanol (CAS NO.3236-48-4):
Empirical Formula: C8H16O2
Molecular Weight: 144.2114 g/mol
Index of Refraction: 1.47
Density: 1.004 g/cm3
Melting point: 61-66 °C
Flash Point: 161.1 °C
Boiling Point: 286.2 °C at 760 mmHg
Vapour Pressure: 0.000303 mmHg at 25 °C
Appearance of Trans-1,4-Cyclohexanedimethanol (CAS NO.3236-48-4): White crystalline powder
Canonical SMILES: C1CC(CCC1CO)CO
InChI: InChI=1S/C8H16O2/c9-5-7-1-2-8(6-10)4-3-7/h7-10H,1-6H2
InChIKey: YIMQCDZDWXUDCA-UHFFFAOYSA-N
Trans-1,4-Cyclohexanedimethanol (CAS NO.3236-48-4) hasn't been listed as a carcinogen by NTP, IARC, ACGIH, or CA Prop 65. And the toxicological properties have not been fully investigated.
Risk Statements: 36
36: Irritating to the eyes
Safety Statements: 39-26
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
39: Wear eye/face protection.
Trans-1,4-Cyclohexanedimethanol ,its cas register number is 3236-48-4. It also can be called 1,4-Cyclohexanedimethanol, trans- . It is hazardous,so the first aid measures and others should be known. Such as: When on the skin: first,should flush skin with plenty of water immediately for at least 15 minutes while removing contaminated clothing. Secondly,Get medical aid. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Then get medical aid soon. While ,it's Inhaled: Remove from exposure and move to fresh air immediately.Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And as soon as to get medical aid. Then you have the ingesting of the product : Wash mouth out with water,and get medical aid immediately.
In addition, Trans-1,4-Cyclohexanedimethanol (CAS NO.3236-48-4) could be stable under normal temperatures and pressures. It is not compatible with strong oxidizing agents, and you must not take it with incompatible materials. And also prevent it to broken down into hazardous decomposition products: carbon monoxide and carbon dioxide.
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