Chemical Properties
clear colorless liquid after melting
Uses
Dimethyl cyclohexane-1,4-dicarboxylate, mixture of cis and trans may be used in chemical synthesis studies.
Uses
1,4-Cyclohexanedicarboxylic Dimethyl Ester is a building block that has been used as a reactant for the preparation of cycloalkylamide derivatives as inhibitors of the soluble epoxide hydrolase.
Flammability and Explosibility
Non flammable
Synthesis
Methanol (500 mL) was cooled to 0°C under ice-salt bath conditions and thionyl chloride (138 g, 4.0 eq.) was added slowly and dropwise. Cis-1,4-cyclohexanedicarboxylic acid (50 g, 1.0 eq.) was added to the above prepared HCl-methanol solution, followed by heating and refluxing the reaction mixture for 1 hour. The reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the solvent was removed by evaporation and the residue was diluted with distilled water and extracted with ethyl acetate (3 x 100 mL). The combined ethyl acetate layers were washed sequentially with saturated NaHCO3 solution and saturated brine and dried over anhydrous Na2SO4. Finally, the solvent was removed by evaporation to give dimethyl 1,4-cyclohexanedicarboxylate (56.4 g, 97% yield) as a white solid.
References
[1] Patent: WO2012/154204, 2012, A1. Location in patent: Page/Page column 83; 84
[2] Journal of Physical Chemistry A, 2010, vol. 114, # 3, p. 1446 - 1456
[3] Patent: WO2012/145569, 2012, A1. Location in patent: Page/Page column 134
