3236-48-4

Basic information

• Product Name: TRANS-1,4-CYCLOHEXANEDIMETHANOL
• Synonyms: trans-4-cyclohexanedimethanol;TRANS-1,4-CYCLOHEXYLENEDIMETHANOL;TRANS-1,4-DI(HYDROXYMETHYL)CYCLOHEXANE;TRANS-1,4-CYCLOHEXANEDIMETHANOL;TRANS-1,4-BIS(HYDROXYMETHYL)CYCLOHEXANE;1,4-CYCLOHEXANEDIMETHANOL (TRANS);trans-1,4-Cyclohexanedimethanol,98%;TRANS-1,4-CYCLOHEXANEDIMETHA
• CAS NO: 3236-48-4
• Molecular Formula: C8H16O2
• Molecular Weight: 144.21
• Product Categories: Chiral Reagents;Intermediates
• Mol File: 3236-48-4.mol
• Article Data: 20

Chemical Properties

• Melting Point: 61-66 °C
• Boiling Point: 283 °C
• Flash Point: >109℃
• Appearance: White/Crystalline Powder
• Density: 1.02
• Vapor Pressure: 0.000303mmHg at 25°C
• Refractive Index: 1.4390 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform, DMSO, Methanol
• PKA: 14.75±0.10(Predicted)
• CAS DataBase Reference: TRANS-1,4-CYCLOHEXANEDIMETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-1,4-CYCLOHEXANEDIMETHANOL(3236-48-4)
• EPA Substance Registry System: TRANS-1,4-CYCLOHEXANEDIMETHANOL(3236-48-4)

Safety Data

• Statements: 36
• Safety Statements: 39-26
• Hazardous Substances Data: 3236-48-4(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline powder

Uses

Intermediate in the preparation of Apadenoson.

InChI:InChI=1/C8H16O2/c9-5-7-1-2-8(6-10)4-3-7/h7-10H,1-6H2/t7-,8-

Synthetic route

trans-1,4-cyclohexylenedimethylene diacetate (10412-78-9) → trans-1,4-Cyclohexanedimethanol (3236-48-4)

Conditions	Yield
With potassium carbonate Ambient temperature;	100%
With sodium hydroxide for 10h; Heating;	46.3%

1,4-cyclohexanedicarboxylic acid (619-82-9) → trans-1,4-Cyclohexanedimethanol (3236-48-4)

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 (180046-62-2) → trans-1,4-Cyclohexanedimethanol (3236-48-4)

Conditions	Yield
With sodium tetrachloroaurate(III) dihydrate In methanol at 20℃; for 2h;	96%

1,4-trans-cyclohexanediyldimethylene dibenzoate (3412-68-8) → trans-1,4-Cyclohexanedimethanol (3236-48-4)

Conditions	Yield
With water; sodium hydroxide In methanol at 70℃;	88.55%

diethyl cyclohexane-trans-1,4-dicarboxylate (19145-96-1) → trans-1,4-Cyclohexanedimethanol (3236-48-4)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether at 20℃; Reduction;	77%

bis-1,4-(hydroxymethyl)cyclohexane (105-08-8) → trans-1,4-Cyclohexanedimethanol (3236-48-4)

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

1,4-cyclohexanedimethylene diacetate (6308-18-5) → trans-1,4-Cyclohexanedimethanol (3236-48-4) + ((1r,4r)-4-(hydroxymethyl)cyclohexyl)methyl acetate + cis-4-(hydroxymethyl)cyclohexylmethyl acetate

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 (3399-22-2) → trans-1,4-Cyclohexanedimethanol (3236-48-4) + (1s,4s)-cyclohexane-1,4-diyldimethanol (3236-47-3)

Conditions	Yield
With methanol; sodium Trennung ueber die Dibenzoyl-Derivate;

cis-dimethyl 1,4-cyclohexanedicarboxylate (3399-21-1) → trans-1,4-Cyclohexanedimethanol (3236-48-4) + (1s,4s)-cyclohexane-1,4-diyldimethanol (3236-47-3)

Conditions	Yield
With methanol; sodium Trennung ueber die Dibenzoyl-Derivate;

trans-1,4-bis-methanesulfonyloxymethyl-cyclohexane (115506-09-7) → 4-methylene-1-cyclohexanemethanol (1004-24-6) + trans-1,4-Cyclohexanedimethanol (3236-48-4)

Conditions	Yield
With potassium hydroxide

polymer, Mn 23500; diketene acetal (3,9-bis(ethylidene)-2,4,8,10-tetraoxaspiro<5,5>undecane); t-cyclohexane-1,4-dimethanol → trans-1,4-Cyclohexanedimethanol (3236-48-4) + pentaerythritol dipropionate

Conditions	Yield
With dichloro-acetic acid; water In 1,4-dioxane-d8 at 37℃; Kinetics; Hydrolysis;

1,4-benzenedicarboxylic acid dimethyl ester (120-61-6) → trans-1,4-Cyclohexanedimethanol (3236-48-4) + (1s,4s)-cyclohexane-1,4-diyldimethanol (3236-47-3)

Conditions	Yield
With hydrogen; aluminum oxyhydroxide; rhodium In ethyl acetate at 22℃; under 760 Torr; for 46h; Title compound not separated from byproducts;

dimethyl 1,4-cyclohexanedicarboxylate (3399-22-2) → trans-1,4-Cyclohexanedimethanol (3236-48-4)

Conditions	Yield
In tetrahydrofuran; (2S)-N-methyl-1-phenylpropan-2-amine hydrate
With copper chromium; hydrogen at 210℃; under 152940 Torr;

terephthalic acid (100-21-0) → trans-1,4-Cyclohexanedimethanol (3236-48-4) + (1s,4s)-cyclohexane-1,4-diyldimethanol (3236-47-3)

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 (1420954-46-6) → trans-1,4-Cyclohexanedimethanol (3236-48-4) + (1s,4s)-cyclohexane-1,4-diyldimethanol (3236-47-3) + (4-methylcyclohexyl)methanol (34885-03-5)

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 (95623-88-4) → trans-1,4-Cyclohexanedimethanol (3236-48-4) + (1s,4s)-cyclohexane-1,4-diyldimethanol (3236-47-3)

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 (1420954-46-6) → trans-1,4-Cyclohexanedimethanol (3236-48-4) + (1s,4s)-cyclohexane-1,4-diyldimethanol (3236-47-3)

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

dimethyl 1,4-cyclohexane dicarboxylate (94-60-0) → trans-1,4-Cyclohexanedimethanol (3236-48-4)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at -20 - 20℃; for 3h; Large scale;

C20H44O2Si2 → trans-1,4-Cyclohexanedimethanol (3236-48-4)

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

(3R,6S)-cyclohex-1-ene-3,6-dimethanol diacetate → trans-1,4-Cyclohexanedimethanol (3236-48-4)

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

(3R,6S)-cyclohex-1-ene-3,6-dimethanol diacetate → trans-1,4-Cyclohexanedimethanol (3236-48-4) + (1s,4s)-cyclohexane-1,4-diyldimethanol (3236-47-3)

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 (107550-83-4) → trans-1,4-Cyclohexanedimethanol (3236-48-4)

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 (107550-83-4) → trans-1,4-Cyclohexanedimethanol (3236-48-4) + (1s,4s)-cyclohexane-1,4-diyldimethanol (3236-47-3)

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

(3R,6S)-cyclohex-1-ene-1,4-dimethanol → trans-1,4-Cyclohexanedimethanol (3236-48-4)

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

(3R,6S)-cyclohex-1-ene-1,4-dimethanol → trans-1,4-Cyclohexanedimethanol (3236-48-4) + (1s,4s)-cyclohexane-1,4-diyldimethanol (3236-47-3)

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

(1R,4S)-cyclohexane-1,4-dimethanol diacetate → trans-1,4-Cyclohexanedimethanol (3236-48-4) + (1s,4s)-cyclohexane-1,4-diyldimethanol (3236-47-3)

Conditions	Yield
With potassium carbonate In methanol at 20℃; for 17h; Overall yield = 1.02 g;	A 0.44 %Spectr. B 82.3 %Spectr.

(1R,4S)-cyclohexane-1,4-dimethanol diacetate → terephthalic acid (100-21-0) + trans-1,4-Cyclohexanedimethanol (3236-48-4) + (1s,4s)-cyclohexane-1,4-diyldimethanol (3236-47-3)

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 (63621-97-6, 81759-81-1) → trans-1,4-Cyclohexanedimethanol (3236-48-4)

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 (63621-97-6, 81759-81-1) → trans-1,4-Cyclohexanedimethanol (3236-48-4) + (1s,4s)-cyclohexane-1,4-diyldimethanol (3236-47-3)

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 (3236-48-4) → trans-1,4-bis-iodomethyl-cyclohexane (83447-96-5)

Conditions	Yield
With 1H-imidazole; iodine; triphenylphosphine In toluene at 60℃; for 2h;	92%

4-(dimethylamino)-1-((3-fluorophenyl)(phenyl)carbamoyl)pyridinium chloride (1187857-70-0) + trans-1,4-Cyclohexanedimethanol (3236-48-4) → ((1r,4r)-4-(hydroxymethyl)cyclohexyl)methyl-3-fluorophenyl(phenyl)carbamate (1187857-71-1)

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 (3236-48-4) + tert-butyldimethylsilyl chloride (18162-48-6) → (±)-trans-[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclohexyl]methanol (180046-62-2)

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%

trans-1,4-Cyclohexanedimethanol (3236-48-4) + ethyl vinyl ether (109-92-2) → C16H30Br2O4

Conditions	Yield
With N-Bromosuccinimide In dichloromethane at 4℃; for 6h;	79%

Isopropenyl acetate (108-22-5) + trans-1,4-Cyclohexanedimethanol (3236-48-4) → trans-1,4-cyclohexylenedimethylene diacetate (10412-78-9) + di-isopropenyl trans-1,4-cyclohexanedimethanol ether + C13H22O3

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 (3236-48-4) → trans-1,4-Bis(bromomethyl)cyclohexane (57702-84-8)

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 (890127-04-5) + trans-1,4-Cyclohexanedimethanol (3236-48-4) → methyl 4-(2-(((trans)-4-(hydroxymethyl)cyclohexyl)methyl)-2H-tetrazol-5-yl)-6-methylpicolinate

Conditions	Yield
With di-tert-butyl-diazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 18h;	67%

trans-1,4-Cyclohexanedimethanol (3236-48-4) → trans-1,4-Bis-cyclohexane (86218-00-0)

Conditions	Yield
With tetrachloromethane; triphenylphosphine	64%

trans-1,4-Cyclohexanedimethanol (3236-48-4) + para-chloroacetophenone (99-91-2) → 1-(4-(((1r,4r)-4-(hydroxymethyl)cyclohexyl)methoxy)phenyl)ethan-1-one

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%

trans-1,4-Cyclohexanedimethanol (3236-48-4) + pivaloyl chloride (3282-30-2) → trans-4-(pivaloyloxymethyl)cyclohexanemethanol

Conditions	Yield
With pyridine at 0℃; for 2h; Esterification;	61%

trans-1,4-Cyclohexanedimethanol (3236-48-4) + benzyl bromide (100-39-0) → (trans-4-((benzyloxy)methyl)cyclohexyl)methanol

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 (1187856-44-5) + trans-1,4-Cyclohexanedimethanol (3236-48-4) → ((1r,4r)-4-(hydroxymethyl)cyclohexyl)methyl (4-chlorophenyl)(phenyl)carbamate (1187856-45-6)

Conditions	Yield
With pyridine Reflux; Large scale;	60%
With pyridine Sealed tube; Reflux;	57%
With pyridine Reflux;

trans-1,4-Cyclohexanedimethanol (3236-48-4) + terephthaloyl chloride (100-20-9) → C24H24O8 (32726-47-9)

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 (3236-48-4) + p-toluenesulfonyl chloride (98-59-9) → trans-4-(hydroxymethyl)cyclohexylmethyl 4-methylbenzenesulfonate (170811-08-2)

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;

trans-1,4-Cyclohexanedimethanol (3236-48-4) + acetyl chloride (75-36-5) → ((1r,4r)-4-(hydroxymethyl)cyclohexyl)methyl acetate

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 (3236-48-4) + phenyl isocyanate (103-71-9) → ((1r,4r)-4-(hydroxymethyl)cyclohexyl)methyl phenylcarbamate (1187856-29-6)

Conditions	Yield
In pyridine at 20℃; for 5h;	51.5%
With pyridine at 20℃; for 5h;

trans-1,4-Cyclohexanedimethanol (3236-48-4) + trans-1,4-cyclohexanedicarboxylic acid dichloride (13170-66-6, 14571-47-2, 19988-54-6) → C24H36O8

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 (3236-48-4) + 3-(1-piperazinyl)-1,2-benzisothiazole (87691-87-0) + methanesulfonyl chloride (124-63-0) → (trans-4-((4-(benzo[d]isothiazol-3-yl)piperazin-1-yl)methyl)cyclohexyl)methyl methanesulfonate

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 (3236-48-4) + methyl iodide (74-88-4) → (4-Methoxymethyl-cyclohexyl)-methanol (110928-47-7)

Conditions	Yield
With potassium hydride	44%

bromoacetic acid tert-butyl ester (5292-43-3) + trans-1,4-Cyclohexanedimethanol (3236-48-4) → tert-butyl 2-(((1r,4r)-4-(hydroxymethyl)cyclohexyl)methoxy)acetate (1187856-42-3)

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 (3236-48-4) → 4-(bromomethyl)cyclohexylmethanol (23791-91-5)

Conditions	Yield
With bromine; triphenylphosphine In N,N-dimethyl-formamide	41%

N-(3-methoxybenzyl)-6-methyl-4-(2H-tetrazol-5-yl)picolinamide (1112181-71-1) + trans-1,4-Cyclohexanedimethanol (3236-48-4) → N-(3-methoxybenzyl)-4-(2-(((trans)-4-(hydroxymethyl)cyclohexyl)methyl)-2H-tetrazol-5-yl)-6-methylpicolinamide (1112174-74-9)

Conditions	Yield
With di-tert-butyl-diazodicarboxylate In tetrahydrofuran for 18h; regioselective reaction;	37%

trans-1,4-Cyclohexanedimethanol (3236-48-4) + ethyl iodide (75-03-6) → 4-(ethoxymethyl)-1-(hydroxymethyl)cyclohexane + 1,4-bis(ethoxymethyl)cyclohexane

Conditions	Yield
With sodium hydride In tetrahydrofuran for 16h; Heating;	A 30% B 32%

Upstream product

• 120-61-6 1,4-benzenedicarboxylic acid dimethyl ester 
• 105-08-8 bis-1,4-(hydroxymethyl)cyclohexane 
• 180046-62-2 (±)-trans-[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclohexyl]methanol 
• 13170-66-6 trans-1,4-cyclohexanedicarboxylic acid dichloride 
• 98837-34-4 ethyl 3-hydroxy-2-methylenebutanoate 
• 140-88-5 ethyl acrylate 
• 3412-68-8 1,4-trans-cyclohexanediyldimethylene dibenzoate 
• 1119-43-3 (E,E)-hexa-2,4-dienedioic acid dimethyl ester 
• 63621-97-6 (2E,4E)-hexa-2,4-diene-1,6-diacetate 
• 107550-83-4 (2E,4E)-hexa-2,4-diene-1,6-diol 
• 94-60-0 dimethyl 1,4-cyclohexane dicarboxylate 
• 1420954-46-6 bis((4-methylcyclohexyl)methyl) cyclohexane-1,4-dicarboxylate 
• 95623-88-4 terephthalic acid 1,4-bis(4-methylcyclohexyl)methyl ester 
• 100-21-0 terephthalic acid 

Downstream Products

• 57702-84-8 trans-1,4-Bis(bromomethyl)cyclohexane 
• 58811-11-3 (trans-4-chloromethyl-cyclohexyl)-methanol 
• 10412-78-9 trans-1,4-cyclohexylenedimethylene diacetate 
• 83447-96-5 trans-1,4-bis-iodomethyl-cyclohexane 
• 175072-42-1 [4-(6-Dimethylamino-purin-9-ylmethyl)-cyclohexyl]-methanol 
• 1187856-42-3 tert-butyl 2-(((1r,4r)-4-(hydroxymethyl)cyclohexyl)methoxy)acetate 
• 1187856-29-6 ((1r,4r)-4-(hydroxymethyl)cyclohexyl)methyl phenylcarbamate 
• 1658500-48-1 tert-butyl (2,6-dichloro-3-(((trans-4-methylcyclohexyl)methyl)amino)pyridin-4-yl)carbamate 
• 1658500-49-2 2,6-dichloro-N³-((trans-4-methylcyclohexyl)methyl)pyridine-3,4-diamine 
• 1616434-24-2 4,6-dichloro-3-(((trans)-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridine 
• 1616434-25-3 2-bromo-4,6-dichloro-3-(((trans)-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridine 
• 1616434-26-4 4,6-dichloro-3-[(trans-4-methylcyclohexyl)methyl]-2-[(3R)-3-phenylmorpholin-4-yl]-3H-imidazo[4,5-c]pyridine 
• 1616434-27-5 6-chloro-4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-2-[(3R)-3-phenylmorpholin-4-yl]-3H-imidazo[4,5-c]pyridine 
• 1616434-28-6 4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-2-[(3R)-3-phenylmorpholin-4-yl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile 

Relevant articles and documents

Calculation of hydrolytic rate constants of poly(ortho ester)s from molecular weights determined by gel permeation chromatography

Purpose. To obtained rate constants from weight-averaged (M(w)) or z-averaged (M(z)) molecular weights for polymers of Schule-Flory distribution and undergoing random scission. These constants were compared with those obtained by parallel 1HNMR studies. Methods. The hydrolysis of two poly(ortho ester)s were followed by 1HNMR and gel permeation chromatography (GPC). Results. Equations to convert number-averaged (M(n)), M(w) and M(z) into fraction of backbone remaining (f(c)) were derived. First-order hydrolytic rate constants of two poly(ortho ester)s; DETOSU-HD and DETOSU-CDM were calculated using these relationships. The rate constants calculated from 1HNMR, M(z) and M(w) were 0.215, 0.218 and 0.182 hr-1, respectively, for DETOSU-CDM and 0.152, 0.086 and 0.038 hr-1 for DETOSU-HD. The large discrepancy in the rates determined by 1HNMR and GPC in the latter case was attributed to that the detector response (refractive index) of the monomers was lower than that of the high molecular weight polymer. The difference is small in the case of DETOSU-CDM, and the rates calculated from GPC data were comparable or nearly identical to that obtained from 1HNMR data. Conclusions. Although GPC can yield rapid and valuable kinetic data for the degradation of biodegradable polymers, the system, however, must be carefully calibrated to account for the variations in Mark-Houwink coefficients and in the response of the mass detector between the high and low MW polymers.

Production of Copolyester Monomers from Plant-Based Acrylate and Acetaldehyde

PCTA is an important copolyester that has been widely used in our daily necessities. Currently, its monomers are industrially produced from petroleum-derived xylene. To reduce the reliance on fossil energy, we herein disclose an alternative route to acces

Synthesis of 1,4-Cyclohexanedimethanol, 1,4-Cyclohexanedicarboxylic Acid and 1,2-Cyclohexanedicarboxylates from Formaldehyde, Crotonaldehyde and Acrylate/Fumarate

Valuable polyester monomers and plasticizers—1,4-cyclohexanedimethanol (CHDM), 1,4-cyclohexanedicarboxylic acid (CHDA), and 1,2-cyclohexanedicarboxylates—have been prepared by a new strategy. The synthetic processes involve a proline-catalyzed formal [3+1+2] cycloaddition of formaldehyde, crotonaldehyde, and acrylate (or fumarate). CHDM is produced after a subsequent hydrogenation step over a commercially available Cu/Zn/Al catalyst and a one-pot hydrogenation/oxidation/hydrolysis process yields CHDA, whereas 1,2-cyclohexanedicarboxylate is obtained by a Pd/C-catalyzed tandem decarbonylation/hydrogenation step.