Abstract
A three-step procedure appropriate for an advanced-level undergraduate organic chemistry laboratory course has been developed for the synthesis of 5-(2-sulfhydrylethyl)salicylaldehyde. Two compounds, namely, 4-(2-iodoethyl)phenol and 5-(2-iodoethyl)salicylaldehyde, are isolated as intermediates from the first two steps of the method. A Grignard reagent is employed as a critical reactant for the synthesis. Several important laboratory techniques, such as TLC, column chromatography, and recrystallization, are emphasized. Spectrometric methods, including GC–MS and NMR spectroscopy, are used to identify the final product as well as the intermediates. Since each step of the procedure involves two or more hours of refluxing, parts of this experiment can be interspersed with other laboratory activities.
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