Nitric Acid → 4,9-Dihydroxydiamantane

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Diamantane 1 (1.28 g, 0.149 mol), CH2Cl2 (250 mL) and 100% HNO3 (90 mL, 2.13 mol) are mixed at 0° C., stirred for 2 h at 25° C. and subsequently diluted with water (180 mL). The CH2Cl2 is removed and the reaction mixture 26 is refluxed for 1.5 h. Removal of the water in the vacuum yielded a mixture of different oligohydroxydes 20 as a remainder. These 20 are added to 200 mL of 96% H2SO4 and stirred for 2 h at room temperature. Subsequently, the reaction mixture is poured onto 300 g ice and filtered. Extraction of the filtrate with one or several organic solvents (typically diethylether) yields 21.3 g (0.097 mmol, 65%) 4.9-dihydroxydiamantane (2, m=0) as white solid, mp. 291-293° C. (from methanol, literature 290-292° C.).

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