Acetic acid (0.774 mL, 13 mmol) and 3-methyl-1-butanol (1.2 mL, 11 mmol) were placed into a 5 mL round-bottomed (rb) flask. The odor of each compound was noted. Four drops of concentrated sulfuric acid were added to the rb flask and the contents were mixed thoroughly. Boiling chips were added and the flask was placed within a reflux apparatus above the hot plate. The contents of the rb flask were heated to a gentle boil such that vapors condensed about one third of the way up the reflux condenser. This resulted in two phases of liquid collecting in the side arm, which were an upper organic phase and a lower water phase. After the reaction refluxed for fifteen minutes, the apparatus was removed from the heat and tipped back so that most of the upper phase in the side arm went back into the reaction flask, and then lowered back into the hot plate. This process was repeated twice more, so that the mixture refluxed for forty-five minutes total. At the end of the third and final reflux period, the apparatus was cooled completely for fifteen minutes. Once cooled, the entire contents of the side-arm were emptied into the rb flask.
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