In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Stereoisomeric biologically active compounds. I. Some conversions of cis-4-chloro-4-cyclohexene-1,2-dicarboxylic acid, published in 1965, which mentions a compound: 610-09-3, mainly applied to , Synthetic Route of C8H12O4.
cf. Baeyer, Ann. Chem. 258, 215(1890); U.S. 1,967,862, CA 28, 5994. To 10 g. cis-4-chloro-4-cyclohexene-1,2-dicarboxylic acid (I) and 60 ml. H2O, under cooling and stirring, a solution of 21 g. KMnO4 in 650 650 ml. H2O was added over 3 hrs. The cooling and stirring was another 2 hrs. and the mixture left standing overnight, yielding meso-butane-1,2,3,4-tetracarboxylic acid m. 191-2°. I (204.5 g.) and 15 ml. concentrated H2SO4 in 500 ml. absolute MeOH was refluxed for 8 hrs. Dimethyl cis-4-chloro-4-cyclohexene-1,2-dicarboxylate (II), b5 148-50°, d204 1.0553, n20D 1.4935 was obtained in 71.3% yield. II (20 g.) and 18 ml. 85% H2NNH2 was refluxed for 3 hrs. Trans-4-chloro-4-cyclohexene-1,2-dicarboxylic acid dihydrazide (III) m. 222-4° (60% EtOH) was obtained in 69.5% yield. To 30 g. III in 105 ml. 10% HCl and 280 ml. CH2Cl2 at 18-20°, a solution of 20.8 g. NaNO3 in 48.5 ml. H2O was slowly added. The nonaqueous layer was dried, filtered, and treated with 160 ml. absolute EtOH. The CH2Cl2 was evaporated, the mixture refluxed for 2 hrs., 210 ml. 40% NaOH added and steam distilled The distillate was acidified with 10% HCl giving the trans-4-chloro-1,2-diamino-4-cyclohexene-2HCl m. 326-8° in 72.1% yield. III (38 g.) and a solution of 26.6 g. NaOH in 350 ml. H2O was refluxed for 12 hrs. and acidified, giving trans-4-chloro-4-cyclohexene-1,2-dicarboxylic acid (IV) m. 115-17° (H2O) in 89.8% yield. IV (10 g.) was oxidized with KMnO4 as described above, giving the dianhydride of dl-butane-1,2,3,4-tetracarboxylic acid m. 172-3°. A solution of 21 g. IV, 8 g. NaOH and 70 ml. H2O was hydrogenated in an autoclave in the presence of 35 g. Ni on Cr2O3 at 100° and 100 atm. The solution was filtered and acidified giving trans-cyclohexane-1,2-dicarboxylic acid (V) m. 220° (Me2O) in 78.2% yield. I (60 g.) and 23.5 g. NaOH in 200 ml. H2O was hydrogenated as described above giving cis-cyclohexane-1,2-dicarboxylic acid (VI), m. 192°, in 92.1% yield. A mixture of 8 g. VI and 20 ml. concentrated HCl was heated in a sealed tube at 180° for 8-10 hrs. and V, m. 220-1°, was obtained in 88.8% yield.
Compound(610-09-3)Synthetic Route of C8H12O4 received a lot of attention, and I have introduced some compounds in other articles, similar to this compound(cis-Cyclohexane-1,2-dicarboxylic acid), if you are interested, you can check out my other related articles.
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