TRANS-2-CARBOMETHOXYCYCLOHEXANE-1-CARBOXYLIC ACID

TRANS-2-CARBOMETHOXYCYCLOHEXANE-1-CARBOXYLIC ACID Property

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

TRANS-2-CARBOMETHOXYCYCLOHEXANE-1-CARBOXYLIC ACID Chemical Properties,Usage,Production

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