The n-propanol (0.82 mL, 11 mmol), propionic acid (0.97 mL, 13 mmol), and concentrated sulfuric acid (4 drops) were added to a 5 mL round-bottomed flask. Contents were mixed thoroughly, and a few boiling chips were added. A distillation apparatus was set up at a 45° angle and the rb flask was heated to a gentle boil on the hot plate. The heating was adjusted so that vapors condensed about ⅓ of the way up the reflux condenser, well above the side arm. After reaction refluxed for 15 minutes, two phases of liquid collected in the side arm, an upper organic phase and a lower water phase. At this point, the apparatus was raised from the heat and tipped so that most of the upper phase in the side arm dripped back into the reaction flask. This process was repeated after 15 minutes. The reaction mixture was allowed to reflux for another 15 minutes (for a total runtime of 45 minutes). Afterwards, the apparatus was allowed to cool for 15 minutes and the entire contents of the side arm were emptied into the flask.
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