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Updated: Aug 15, 2026

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
Published on: October 30, 2018
Simple preparation of 3I-O-substituted beta-cyclodextrin derivatives using cinnamyl bromide
Jindrich Jindrich1, Iva Tislerová
1Department of Organic Chemistry, Charles University, Faculty of Science, Prague, Czech Republic. jindrich@natur.cuni.cz
Abstract:
[reaction: see text] A new method for preparation of 3(I)-O-substituted beta-cyclodextrin derivatives was developed. Cinnamyl bromide reacts with beta-cyclodextrin to form predominantly the 3(I)-O-cinnamyl derivative (30% isolated yield, >90% regioselectivity). After protection of the remaining cyclodextrin hydroxyls by acetylation, the cinnamyl group can be easily transformed to many other groups (exemplified by transformation to 3(I)-O-carboxymethyl derivative). Substitution pattern in singly modified CDs was unambiguously determined by a combination of 2D NMR techniques.
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