Synthesis and Use of Ethyl 6-Acetyloxyhexanoate as an Internal Standard: An Interdisciplinary Experiment for an Undergraduate Chemistry Laboratory

The combination of organic synthesis and analytical chemistry into a related laboratory experiment is an excellent demonstration of the utility of making a compound to then be used further. Herein we describe an undergraduate laboratory experiment that involves the straightforward synthesis of an internal standard, ethyl 6-acetyloxyhexanoate, for the quantification of various aroma compounds in juice through GC-FID analysis. In addition to the organic synthetic procedures of undertaking a reaction under reflux, separation, and extraction protocols followed by determining the purity of a synthesized compound, this experiment also facilitates the teaching of making standard solutions, using solid phase extraction, preparing samples, and performing and interpreting the results of GC-FID analysis.