The Effects of Intramolecular Hydrogen Bonding on the Reaction of Phenols with Epoxide in the Presence of Nano Calcium Carbonate

Abstract

The reaction of phenols and dihydroxybenzenes with epoxide in the presence of nano CaCO₃ was studied. Catechol could react with epoxide and gave monochlorohydrin derivative; other dihydroxybenzenes and monomeric phenols had no reaction under the same conditions. The reaction of catechol with epoxide did not occur when nano CaCO₃ was replaced by a normal one. These were attributed to the strong interaction between nano CaCO₃ and the substrate as catechol possessed intrahydrogen bond and excess active hydrogen, which can induce the intramolecular proton transfer via the intramolecular hydrogen bond and promote the reaction of hydroxyl and epoxide. This is an example revealing the unique role of the hydrogen bond played in chemical reactions.

Keywords:

• Hydrogen bond
• Phenol
• Epoxide
• Nano CaCO₃

Acknowledgements

We thank the financial support given by the National Natural Science Foundation of China (Grant No. 20272044).