Structural Identification of Products from the Chloromethylation of Salicylaldehyde

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.

Synthesis and Structure of an Aqueous Stable Europium-Based Metal–Organic Framework with Ratiometric Fluorescence Sensing for Phosphate and Luminescence Quenching for Salicylaldehyde

“…Salicylaldehyde is an extremely versatile fine chemical product, which is widely used in the synthesis of pesticides, medicines, fragrances, chelating agents, dye intermediates, etc. 22 Salicylaldehyde is also used in the electroplating industry as a brightener and leveling agent, and low concentrations of salicylaldehyde are often used as a preservative in flavors and fragrances because of its potent ability to reduce bacterial activity. However, it is volatile, is unsafety to the human body, and pollutes air and water bodies, and thus, it is very important to be quickly detected.…”