Fischer esterification is an established synthetic method for producing esters and is a prevalent experiment in many organic laboratory manuals. This study, which is part of a larger investigation producing various hexyl acetates, specifically utilizes the acid-catalyzed reaction of acetic acid with 4-methyl-2-pentanol. The reaction was executed using different reflux time periods in an effort to determine the optimal time requirements necessary to produce the ester, 4-methyl-2-pentyl acetate. The product mixtures were separated by extraction, dried, and then purified by distillation at atmospheric pressure. The purity of the acetate products were determined using gas-liquid chromatography, and microboiling point and refractive index determinations were made for comparison to the reported theoretical values. Mass spectrometry and infrared spectroscopy were utilized to help determine the product identity, however, it was nuclear magnetic resonance spectrometry experiments, both 1D and 2D, that ultimately provided spectral identities. The NMR techniques used included PMR, CMR, Gated-Decoupled CMR, DEPT45, DEPT90, DEPT135, DEPTQ135, COSY, HSQC, HMBC, and TOCSY experiments.

Fischer esterification of 4-methyl-2-pentanol

254th National Meeting (2017)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.