The cis–trans transformation of cyclohexane formic acid ester compounds

Abstract

Trans-alkyl cyclohexane formic acid phenol ester compounds are synthesised by reaction of trans-cyclohexane formic acid and phenols. This process also produces many harmful cis-alkyl cyclohexane formic acid phenol ester compounds that are harmful to the environment. Using p-toluenesulphonic acid as the catalyst in this experiment, these cis compounds were transformed to their trans form. The yields of trans-alkyl cyclohexane formic acid phenol ester compounds were more than 70%, which was significantly higher when compared to the yields of 40–60% obtained using the control method. The effects of catalyst, reaction time and reaction temperature on cis–trans transformation were investigated. The possible mechanism of cis–trans transformation has been discussed in this report.

Keywords:

• cyclohexane formic acid
• cis–trans transformation
• cyclohexane formic acid phenol ester
• synthesis

Acknowledgements

Financial support for this work was received from the international cooperation projects of Shaanxi Province (kw-43). We also want to thank the Fundamental Research Funds for the Central Universities in China (61). Editorial help of Prof C. Chen at the University of Queensland, Australia, is acknowledged.