1,3-Cyclohexanedicarboxylic acid

1, 3-cyclohexanedicarboxylic acid PREPARATION a To a suspension of isophthalic acid (500 g, 3 mol) in methanol (2.8 l) was added 5percent Rhodium-on-alumina catalyst (50 g) and acetic acid (150 ml).The reaction mixture was shaken under hydrogen (50 psi) at room temperature overnight.The mixture was filtered through celite.To this solution was added fresh 5percent Rhodium-on-alumina catalyst (25 g), and the mixture was shaken under 50 psi of hydrogen for another 24 hours.The final reaction mixture was filtered through celite.The solution was concentrated under vacuum to give 493 g of the title compound as a white powder (96.3percent yield).m.p. 163-165° C. To a suspension of isophthalic acid (5.0 g, 30.1 mmol) in 45 ml of acetic acid was added a slurry of 0.1 g of platinum oxide in 5 ml of acetic acid.The resulting mixture was stirred under 50 psi of hydrogen at 25° C. for 16 hours. NMR analysis (DMSO-d6) at this time showed complete reduction of starting material.The reaction mixture was filtered through Celite and the filter cake was rinsed with methanol.The combined filtrate and washes were concentrated under reduced pressure, using heptane to azeotropically remove residual acetic acid.Trituration of the resultant semi-solid with heptane and filtration of the precipitate provided 4.92 g (95percent) of the title compound as a white powder. PREPARATION u A 100 mL stainless steel-made autoclave equipped with a stirrer was charged with 25.1 g of isophthalic acid, 2.8 g of a catalyst (10percent Pd/C, manufactured by NE Chemcat Corporation), and 100 mL of water. The autoclave was purged with nitrogen introduced from the autoclave nozzle inlet three times at 5 MPa, and the mixture was heated to 150° C. while stirring at 400 rpm under normal pressure. [0163] When the temperature reached 150° C., hydrogen supply was started intermittently to achieve a pressure of 3.5 MPa, and the reaction was performed until there is no hydrogen absorption. [0164] After the completion of reaction, the product was cooled to room temperature. The reaction mixture was taken out, and after a 5N aqueous NaOH solution containing sodium hydroxide of 2.5 times mol the charged isophthalic acid amount was added thereto, the mixture was filtered to remove the catalyst. [0165] The filtrate was neutralized with a 5N aqueous HCl solution, and then analyzed by high-performance liquid chromatography. It was found that the conversion of isophthalic acid was 100percent, and the yield of 1, 3-cyclohexanedicarboxylic acid was 99percent.In a 50 L autoclave, 10 kg of isophthalic acid, 30 kg of water and 0.3 kg of a 5percent ruthenium-carbon catalyst were added, and the mixture was purged once with nitrogen and then with hydrogen three times. Turn on stirring, hydrogen pressure to 2MPa, heating to 100 degrees, began to hydrogen absorption, and gradually warming to 120 degrees, maintaining the temperature until no hydrogen absorption so far. Sampling monitoring, high performance liquid chromatography (HPLC) analysis, the raw material isophthalic acid reaction completely. Drop to room temperature, drain hydrogen, nitrogen once. The catalyst was filtered off, and the water in the reaction mixture was distilled off to obtain a viscous product. 10 L of methanol was added and the mixture was stirred for beating to obtain a white powder with good dispersibility. Filtration and drying afforded 10 kg of 1, 3-cyclohexanedicarboxylic acid with a cis content of 80percent.Example 6 5, 5'-(cyclohexane-1, 3-diyl)bis(1, 3, 4-thiadiazol-2-amine) (I-31) A mixture of A mixture of cyclohexane-l, 3-dicarboxylic acid (1.0 equivalent) and thiosemicarbazide (2.0 equivalents) were taken in POCI3 (6.0 equivalents) and stirred at 80 C for 3 h. The reaction mixture was cooled to room temperature and poured on to ice. The resulting mixture was filtered and then brought to pH 8 using KOH. The white solid that was formed washed with water and dried to afford the desired product (31) in 56 % yield. This material was used as such for the next step.5, 5'-(cyclohexane-l, 3-diyl)bis(l, 3'4-thiadiazol-2-amine) (1-31): A mixture of cyclohexane-l, 3-dicarboxylic acid (1.0 equivalent) and thiosemicarbazide (2.0 equivalents) were taken in POCI3 (6.0 equivalents) and stirred at 80 C for 3 h. The reaction mixture was cooled to room temperature and poured on to ice. The resulting mixture was filtered and then brought to pH 8 using KOH. The resulting material that was formed washed with water and dried to afford the desired product (31). This material was used as such for the next step.A mixture of cyclohexane-l, 3-dicarboxylic acid (1.0 equivalent) and thiosemicarbazide (2.0 equivalents) were taken in POCI3 (6.0 equivalents) and stirred at 80 C for 3 h. The reaction mixture was cooled to room temperature and poured on to ice. The resulting mixture was filtered and then brought to pH 8 using KOH. The resulting material that was formed washed with water and dried to afford the desired product (31). This material was used as such for the next stepA four-neck flask equipped with a stirrer, a gas inlet tube, a thermometer, a gas purge line, and a condenser was charged with 15.1 g of A four-neck flask equipped with a stirrer, a gas inlet tube, a thermometer, a gas purge line, and a condenser was charged with 9.1 g of A four-neck flask equipped with a stirrer, a gas inlet tube, a thermometer, a gas purge line, and a condenser was charged with 75.3 g of The metal-supported catalyst obtained in Preparation Example 1,

Molecular Weight:172.18
XLogP3:0.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:172.07355886
Monoisotopic Mass:172.07355886
Topological Polar Surface Area:74.6
Heavy Atom Count:12
Complexity:179
Undefined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes