On the Separation of Acidic and Neutral Substances 3 grams of a mixture containing equal proportions of benzoic acid, 2-naphthol, and 2-methoxynaphthalene was dissolved in 30 ml of ether, 10 ml of water, and 10 ml of 10% aq sodium bicarbonate in a separatory funnel. The lower layer, containing benzoic acid, was drained. 10 ml of 5% aq sodium hydroxide was added to the funnel, and the lower layer, containing 2-naphthol, was drained. 5 ml of water was added to the funnel, and the lower layer, containing 2-naphthol, was added to the previously-drained 2-naphthol solution. 15 ml of saturated aq sodium chloride was added to the funnel, and the lower layer was discarded. The remaining ether layer contained 2-methoxynaphthalene. The benzoic acid solution was acidified with concentrated hydrochloric acid, and cooled in an ice bath. Vacuum filtration was performed, and the crude product was re-crystallized from boiling water. The 2-naphthol solution was acidified with concentrated hydrochloric acid, and cooled in an ice bath. Vacuum filtration was performed, and the crude product was re-crystallized from boiling water. 4 grams of anhydrous sodium sulfate was added to the 2-methoxynaphthalene solution. The solution was decanted into a tared flask, and the ether was evaporated. The crude 2-methoxynaphthalene was re-crystallized from methanol.
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