[CH:1]1[C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11](I)=[CH:10][CH:9]=2)=[CH:5][CH:4]=[C:3](I)[CH:2]=1.[OH-:16].[Na+].[O-:18][O-].[Na+].[Na+]>[Cu].O>[CH:2]1[C:3]([OH:16])=[CH:4][CH:5]=[C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([OH:18])=[CH:10][CH:9]=2)[CH:1]=1In a 0.5-liter three-neck flask equipped with stirrer, thermometer, and ball condenser, 84.4 g (0.2 mole) of 4,4'-diiododiphenyl ether, 93.0 g (2.32 moles) of NaOH, 2.1 g of powdered copper, 1.7 g of cuprous chloride, 3.3 g of sodium peroxide, and 33 ml of water were heated over 4 hours to 190° C. After cooling to 140° C., another 37 ml of water were added and the batch was stirred for another 3 hours at 150° C. After cooling to room temperature, the batch was mixed with 200 ml of water and filtered. 200 g of ice were added to the filtrate, which was acidified with concentrated hydrochloric acid. The precipitated 4,4'-dihydroxydiphenyl ether was drawn off by suction and recrystallized from 0.8 liter of water. Yield: 33.5 g (83%).
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