Synlett 2019; 30(01): 44-48
DOI: 10.1055/s-0037-1610334
letter
© Georg Thieme Verlag Stuttgart · New York

Structural Identification of Products from the Chloromethylation of Salicylaldehyde

Ebrahim Kadwa
,
Holger B. Friedrich
,
School of Chemistry and Physics, University of KwaZulu-Natal, Private Bag X54001, Durban 4000, South Africa   Email: bala@ukzn.ac.za
› Author Affiliations
This project is generously supported by the c* change PAR program, the National Research Foundation, and the University of KwaZulu-­Natal, for which we are grateful.
Further Information

Publication History

Received: 16 October 2018

Accepted after revision: 30 October 2018

Publication Date:
26 November 2018 (online)

Abstract

In the functionalization of salicylaldehyde to give 5-(chloromethyl)salicylaldehyde, two byproducts [5-(hydroxymethyl)salicylaldehyde and 5,5′-methylenebis(salicylaldehyde)] were also isolated. ­Detailed characterizations and structural analyses of all three products by single-crystal X-ray diffraction, multinuclear NMR spectroscopy, high-resolution mass spectrometry, and IR spectroscopic techniques are presented and discussed. A strategy is presented for the preferential isolation of the two byproducts through column chromatography.

Supporting Information

 
  • References and Notes

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  • 23 CCDC 1862047, 1862048, and 1862049 contain the supplementary crystallographic data for compounds 2–4, respectively. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures. Tables of selected data collection and refinement information, bond lengths and angles, and hydrogen-bonding interactions are also available in the Supporting Information.
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