Water → HCID 21746791, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, 2-decanoyl-6-methoxynaphthalene (9.4 g, 30 mmol) and potassium hydroxide (67 g, 1.2 mol) were dissolved in hydrazine monohydrate (70 ml, 1.4 mol) and diethylene glycol (200 ml). The solution was refluxed for 17 hours, and water (36 ml) was added. Under a stream of nitrogen, the solution was distilled to distill away an excessive amount of hydrazine and water. Further, the solution was refluxed under a nitrogen atmosphere for 41 hours. Subsequently, while using an ice bath, the solution was cooled by putting ice into the reaction solution, hydrochloric acid was slowly added until the solution became neutral. The reaction solution was extracted with ether (100 ml×3), and the obtained organic layer was washed with saturated saline water (100 ml×5). The organic layer was dried with anhydrous magnesium sulfate, and filtered. Then, the solvent was distilled away under reduced pressure. The obtained brown solid was recrystallized from hexane to obtain 6-decyl-2-hydroxynaphthalene (7.3 g, 90%) as a white solid.

Provenance & Evidence