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Dihydroxybenzophenone.7-Sixty-five grams of catechol dibenzoate, 185 ml. of nitrobenzene and 56 g. of anhydrous aluminum chloride were heated on the steambath for six hours. Ice and hydrochloric acid were then added, and, after the decomposition was complete, the nitrobenzene was steam distilled. The remaining solution was chilled and the solid material collected, dried and dissolved in 400 ml. of methanol. The resulting solution was saturated with anhydrous hydrogen chloride, and refluxed for 3.5 hours. Methanol was removed on the steam-bath, water was added to the residue, and the mixture was steam distilled to remove methyl benzoate. The residual mixture was boiled, enough water was introduced to effect solution, and decolorizing charcoal was added. After being boiled for several minutes, the solution was filtered and chilled. The product was collected and recrystallized four times from hot water. The resulting colorless crystalline material melted at 147-148°, and showed no melting point depression when mixed with an authentic specimen.7 The

Reactions of Hydrogen Azide with Alicyclic Alcohols 3287 decomposed at 290-295°; recrystallized from ethanolwater, it decomposed at 295°. Both samples burned in a flame leaving a grayish residue which when moistened with distilled water tested alkaline to litmus. Both samples and acetylacetone gave the same derivatives with 2,4-dinitrophenylhydrazine, melting at 122°( lit.122°).13Crude Yr melted at 38-40°, recrystallized from low boiling Skellysolve, m.p. 43°( lit. 43°6). After boiling with water, it gave the derivative of acetylacetone with 2,4-dinitrophenylhydrazine, melting at 122°. Allylacetylacetone (VI).-Similarly, 140 g. (1 mole) of VI was treated with 3.5 moles of sodium acetylide. Fractionation of the products gave 14 g., 20% yield, of allylacetone, b.p. 69°at 100 mm., w25d 1.4178; 2,4-dinitrophenylhydrazone, m.p. 103-104°( lit. 104°14); 39 g., 36%,, of unreacted VI, b.p. 82-84°at 16 mm., derivative with 2,4-dinitrophenylhydrazine, m.p. 185-186°, and a residue of 56 g., 56%yield, of crude allylacetylacetone amine (VIII), m.p. 63-66°, recrystallized from low boiling Skellysolve, m.p. 65-67°; derivative with 2,4-dinitrophenylhydrazine, m.p. 185-186°.On heating VIII with 10% sodium hydroxide, ammonia was (13) R. L. Shriner and R. C. Fuson, "Identification of Organic Compounds," 3rd ed.,