Nitric Acid → HCID 13066911, compound

Participants

Reaction Steps

Dioxane (15 ml) was added to 1,4-dimethoxy-2-methyl-3-[(12-hydroxy-5,10-dodecadiynyl)]naphthalene (II, 0.57 g, 1.5 mmole) and silver oxide (0.74 g, 6.0 mmole), and the mixture was stirred under cooling with ice. 6 N nitric acid (1.5 ml) was added to the mixture over a 5-minute period and, 5 minutes later, the ice bath was taken off, followed by stirring at room temperature for 30 minutes. Water (20 ml) was added to the reaction solution, and the dioxane was distilled off under reduced pressure. Ethyl acetate (50 ml) was added to the residue, and the insolubles were filtered out. The organic layer was separated out, washed with water and dried (over MgSO4), followed by distilling off the solvent under reduced pressure. The crystals precipitated were recrystallized from isopropyl ether, thereby yielding the desired 2-methyl-3-(12-hydroxy-5,10-dodecadiynyl)-1,4-naphthoquinone (I, 0.47 g, 90%).

Provenance & Evidence