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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 35, 2005 - Issue 4
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Original Articles

Synthesis of Photochromic Monomers Derived from 1′‐(2‐Methacryloxyethyl)‐3,3‐Dimethyl‐2‐[2H]‐Spirobenzopyran Indoline

, &
Pages 603-610 | Received 17 Nov 2004, Published online: 12 Apr 2011
 

Abstract

The syntheses of five photochromic monomers derived from N‐ (2‐methacryloxyethyl)‐3′, 3′‐dimethylspiro‐[2H‐1] benzopyrane‐2, 2′‐indoline are reported. The preparation of these compounds involves the heterogeneous reaction between the N‐(hydroxyethyl)‐2,3,3‐trimethylindolenonium bromide and methacryloyl chloride in a polar solvent. The esterificated salt is easily purified by crystallization in chloroform‐hexane. Further condensation with the proper 2‐hydroxybenzaldehyde produces the photochromic monomer in high yield. This method can also be applied in the preparation of other spiropyrane derivatives.

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