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Synlett 2019; 30(01): 44-48
DOI: 10.1055/s-0037-1610334
DOI: 10.1055/s-0037-1610334
letter
Structural Identification of Products from the Chloromethylation of Salicylaldehyde
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.Weitere Informationen
Publikationsverlauf
Received: 16. Oktober 2018
Accepted after revision: 30. Oktober 2018
Publikationsdatum:
26. November 2018 (online)
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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.
Key words
salicylaldehyde - chloromethylation - chloromethylsalicylaldehyde - crystal structure - hydroxymethylsalicylaldehyde - methylenebissalicylaldehydeSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610334.
- Supporting Information
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References and Notes
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