Alternative and Eco-Friendly Synthesis of Tetrakis(Aminomethyl)Calix-[4]-Resorcinarene

Authors: S. Ali Moussaoui, Ziad Damaj, Moheddine Wehbie, Stéphane Pellet Rostaing, Iyad Karamé

A cleaner and eco-friendly method was developed for the preparation of tetrakis(aminomethyl)calix-[4]-resorcinarene via a synthetic pathway of five steps starting from methylresorcinol. This alternative methodology is firstly based on avoiding the use of CH2BrCl, which is a non-eco-friendly substance with high ozone depletion potential, and on replacing it by CH2Cl2 as a readily available reagent with much less dangerous effects. Secondly, this method engages acetone or CH2Cl2 as the solvent of the bromination step in the place of the very toxic CCl4, leading to tetrakis(bromomethyl)calix-[4]-resorcinarene. The brominated intermediate has been reacted with sodium azide in acetone instead of the high-boiling solvent DMSO to produce tetrakis(azidomethyl) calix-[4]-resorcinarene without the need of tedious purification. Lastly, this work reports an efficient hydrogenation method of the versatile azido adduct employing Pt/C (5%) as the catalyst for the preparation of the amino cavitand as an alternative route with high atom economy that can replace the classical methods used currently.


Journal: International Journal of Organic Chemistry
DOI: 10.4236/ijoc.2017.74032 (PDF)
Paper Id: 81102 (metadata)

See also: Comments to Paper

About scirp

(SCIRP: is an academic publisher of open access journals. It also publishes academic books and conference proceedings. SCIRP currently has more than 200 open access journals in the areas of science, technology and medicine. Readers can download papers for free and enjoy reuse rights based on a Creative Commons license. Authors hold copyright with no restrictions. SCIRP calculates different metrics on article and journal level. Citations of published papers are shown based on Google Scholar and CrossRef. Most of our journals have been indexed by several world class databases. All papers are archived by PORTICO to guarantee their availability for centuries to come.
This entry was posted in IJOC. Bookmark the permalink.

Leave a Reply

Your email address will not be published. Required fields are marked *