TRANS-2-CARBOMETHOXYCYCLOHEXANE-1-CARBOXYLIC ACID Chemical Properties

Boiling point:

72-75 °C(Press: 0.5-0.75 Torr)

Density 

1.191±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

4.43±0.28(Predicted)

Appearance

White to off-white Solid

TRANS-2-CARBOMETHOXYCYCLOHEXANE-1-CARBOXYLIC ACID Usage And Synthesis

Synthesis

General procedure for the synthesis of trans-2-(methoxycarbonyl)cyclohexanecarboxylic acid from methanol and cis-1,2-cyclohexanedicarboxylic anhydride: 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 for 1 hour at 100 °C. Upon completion of the reaction, the solvent was removed by evaporation to afford a white solid product, trans-2-(methoxycarbonyl)cyclohexanecarboxylic acid (8.46 g, 45.5 mmol, 100% yield), which could be used in subsequent steps without further purification. The melting point of the product was 67-69 °C. Infrared spectra (KBr) showed characteristic absorption peaks: ν 3060, 1710, 1670 cm-1. 1H NMR (400 MHz, CDCl3) data: 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 (m, 2H), 1.83-1.72 (m, 2H). 1.61-1.36 (m, 4H).13C NMR (100 MHz, CDCl3) data: δ 179.76, 174.06, 51.71, 42.48, 42.33, 26.25, 25.95, 23.74, 23.62.High-resolution mass spectrometry (ESI) analysis: [M-H]-calculated value for C9H13O4 of 185.0792 and the measured value was 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

TRANS-2-CARBOMETHOXYCYCLOHEXANE-1-CARBOXYLIC ACID(2484-60-8)Related Product Information

• trans-1,2-Cyclohexanedicarboxylic acid
• TRANS-2-CARBOMETHOXYCYCLOHEXANE-1-CARBOXYLIC ACID
• dimethyl cyclohexane-1,2-dicarboxylate
• (1S,2S)-1,2-CYCLOHEXANEDICARBOXYLIC ACID
• SUBERIC ACID MONOMETHYL ESTER