1-Nitronaphthalene [86-57-7-A] C10H7NO2
In a 1000 ml three-neck flask, place 76 ml of 60% nitric acid, 174 ml of 80% sulfuric acid, and 128 g of powdered naphthalene. The flask is equipped with a KPG stirrer, Dimroth condenser, and a thermometer (up to 100 °C). The reaction mixture is heated in a water bath to 50 °C for 6 hours with stirring, then for another 2 hours at 60 °C. During this time, 1-nitronaphthalene separates as an oily liquid on the surface. The contents of the flask are transferred to a 2000 ml beaker containing 1000 ml of water. The crude product solidifies immediately, is sharply suctioned off, freed from acid residues by repeated melting with boiling water, and precipitated as granules during the last boiling step with cold water. For further purification, recrystallization from petroleum ether is performed. The yield is 95% of the theoretical yield of a product melting at 61 °C.
Description: 1-Nitronaphthalene forms shiny, yellow needles from ethanol or petroleum ether, insoluble in water. The substance dissolves in concentrated sulfuric acid with a red color. 1-Nitronaphthalene is needed for a significant number of chemical syntheses, such as the production of 1-naphthylamine.
Source: Fierz-David, Blangey - Fundamental Processes of Dye Chemistry, Interscience, New York, 1949
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Last updated: 20/09/2005
Other name: α-Nitronaphthalene