Synthesis
The cis-1,2-cyclohexanedicarboxylic anhydride (7.0 g, 45.5 mmol) was dissolved in methanol (2 mL, 49.5 mmol) and the reaction was stirred at 100 °C for 1 hour. Upon completion of the reaction, the solvent was removed by evaporation to afford trans-2-(methoxycarbonyl)cyclohexanecarboxylic acid (8.46 g, 45.5 mmol, 100% yield) as a white solid, which could be used in subsequent steps without further purification. The melting point of the product is 67-69 °C. Infrared spectrum (KBr): ν 3060, 1710, 1670 cm-1. 1H NMR (400 MHz, CDCl3): δ 7.54 (s, 1H), 3.68 (s, 3H), 2.89-2.81 (m, 2H), 2.09-1.96 (m, 2H), 1.83-1.72 (m, 2H), 1.61-1.36 （13C NMR (100 MHz, CDCl3): δ 179.76, 174.06, 51.71, 42.48, 42.33, 26.25, 25.95, 23.74, 23.62. High-resolution mass spectrometry (ESI): Calculated value of C9H13O4 [M-H]- 185.0792, measured value of 185.0790. 185.0790.
References
[1] Letters in Organic Chemistry, 2018, vol. 15, # 5, p. 404 - 411
[2] Journal of Organic Chemistry, 2008, vol. 73, # 6, p. 2454 - 2457
[3] Organic and Biomolecular Chemistry, 2011, vol. 9, # 22, p. 7929 - 7940
[4] Patent: US2014/288314, 2014, A1. Location in patent: Paragraph 197; 198
[5] Chirality, 2015, vol. 27, # 10, p. 693 - 699
