Hydrochloric Acid → 2,5-Dihydroxyterephthalonitrile

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[C:1]([C:3]1[CH:8]=[C:7]([O:9]C)[C:6]([C:11]#[N:12])=[CH:5][C:4]=1[O:13]C)#[N:2].[Br-].[Br-].[Br-].[Al+3].Cl>C1C=CC=CC=1>[C:1]([C:3]1[CH:8]=[C:7]([OH:9])[C:6]([C:11]#[N:12])=[CH:5][C:4]=1[OH:13])#[N:2]

참가 물질

실험 절차

In a 5 liter-reaction vessel, 100 g (5.32×10-1M) of 2,5-dicyano-1,4-dimethoxybenzene, 312.5 g (1.17M) of anhydrous aluminum tribromide and 2.5 liters of dry benzene were placed, followed by heat-refluxing for 7 hours. After the reaction, the reaction mixture as cooled and poured into a mixture of 3 kg of crushed ice and 500 ml of concentrated hydrochloric acid to precipitate a crystal. The crystal was recovered by filtration and dissolved in 2N-sodium hydroxide aqueous solution. The resultant insoluble residue was filtered off and the filtrate was acidified with 2N-hydrochloric acid to precipitate a crystal. The crystal was recovered by filtration and washed with water, followed by drying to obtain 35.5 g of 2,5-dicyanohydroquinone (Yield: 41.7%).