Procedure: Nucleophilic displacement - Formation of an ether by an SN2 reaction

To a 10 mL round bottom flask sodium hydroxide (0.064 g, 1.60 mmol), 2-naphthol (0.200 g, 1.39 mmol), and a few boiling stones were added. Next, absolute ethanol (3 mL) was added and the air condenser was attached. The mixture was refluxed for 25 min while the sand bath was at 30% heat and cooled for 3 min. Then, n-butyl iodide (0.200 mL) was added to the mixture through the top of the condenser and reflux continued for 1 h. After reflux was complete, the reaction mixture was poured over ~10 g of ice in a beaker. The round bottom flask was then rinsed with cold water (2 x 1.0 mL) and this was transferred to the reaction mixture. The reaction mixture was stirred with a glass rod until 95% of the ice melted and the final product (0.036 g, 13.6% yield) was collected via suction filtration after being rinsed with ice water. A small portion of the product was then analyzed using thin layer chromatography and different solvent systems of ethyl acetate and hexanes were experimented with until a decent separation between starting material and product was seen.