Propanoic acid (0.98 mL, 13 mmol), 3-methyl butanol (1.2 mL, 11 mmol), boiling chips, and concentrated sulfuric acid (four drops) were added to a round-bottomed (rb) flask. The mixture was refluxed for 45 minutes, while water was removed from the reaction via condensation collection in the side arm. The product was washed with water (1 mL). The solution was then backwashed with aqueous sodium bicarbonate (1 mL) and aqueous sodium chloride (1 mL). The product (1.24 g, 8.6 mmol, 78%) that had an apple-like odor was dried with CaCl2 pellets, and then tested using infrared spectroscopy.
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