Application of 1687-29-2, These common heterocyclic compound, 1687-29-2, name is Cis-dimethyl cyclohexane-1,2-dicarboxylate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
SOCl2 (15.45 g, 129.8 mmol) was added to a mixture of cis-1,2-cyclohexanedicarboxylic anhydride (200 g, 1298 mmol) and methanol (1400 mL) at 20 °C.There ac-tion mass was refluxed for 3?4 h. Methanol was concentrated completely, the residue was diluted with methyl-tert-butyl ether(MTBE, 1000 mL), sodium bicarbonate solution was added to it. The organic layer was separated and washed with water and brine solution. The organic layer was distilled completely to furnish 8. The residue was dissolved in fresh methanol (1040 mL), and sodium methoxide (28 g, 519.4 mmol) was added. The reaction mass was refluxed for 4h, and methanol was distilled completely under reduced pressure. To the residue, 13percent aqueous NaOH solution (2000 mL)was added. Reaction mass was maintained for 3?4 h at 75 °C and cooled to 0?5 °C. The reaction mass pH was adjusted to 2.0 at 0?5 °C with concentrated HCl (900 mL). The obtained solid was filtered and the wet cake was washed with excess water (1500 mL) and dried under reduced pressure to give a white solid. Yield: 87percent. HRMS (ESI TOFMS): calcd. for C8H12O4Na, 173.0814; found, 173.0821. HPLC conditions: chemical column: Zorbax SB CN (150×4.6 mm)×(3.5mu); mobile phase: A: 0.1percent H3PO4 in H2O/MP; B: ACN, purity by HPLC (area under curve): 94.3percent; (trans) retention time: 6.98 and 2.1percent; (cis) retention time: 7.579. Chiral column: Chiral PAK IC (250×4.6 mm) 5.0 mum; mobile phase: n-hexane/IPA/TFA (950:50 l:1); diluent: methanol/MP (1:1); flow rate: 1.0 mL/min; column temperature: 25 °C; inj. vol.: 10 mul. Wave length: 210 nm. Purity by HPLC (area under curve) 40.35percent (R,S isomer), retention time 16.065; and 56.18percent (R,S isomer) retention time 20.269.
The synthetic route of 1687-29-2 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Ravi Ganesh; Pachore, Sharad S.; Pratap; Umesh; Basaveswara Rao; Murthy; Suresh Babu; Synthetic Communications; vol. 45; 23; (2015); p. 2676 – 2682;,
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