Hydrochloric Acid → Phenol, 2,2′-[oxybis(2,1-ethanediyloxy)]bis[4-amino-

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Reaction Conditions

Reaction Steps

In a 600 ml glass beaker, 13.9 g (0.08 mole) of sulfanilic acid were dissolved in 41 ml of 10% sodium hydroxide solution and a solution of 5.7 g (0.08 mole) of sodium nitrite in 30 ml of water was added to the resulting solution. After the mixture had been cooled to 0-5° C., 72 ml of 10% hydrochloric acid were added dropwise over a period of 45 minutes. This cold diazonium solution was then added dropwise over a period of 30 minutes at 0-5° C. to a solution of 11.8 g (0.04 mole) of bis-([-2-(2-hydroxyphenoxy)-ethyl]-ether (prepared in accordance with J. Am. Chem. Soc. (1977), 2568) in 66 ml of 10% sodium hydroxide. After stirring for another 1.5 hours at 15° C., 38.3 g (0.22 mole) of sodium dithionite were added. The mixture was then heated for 20 minutes to 75° C., the product precipitating. After cooling, the product was filtered off under suction, washed with water and dried in vacuo at 70° C. The product had a melting point of 215° C. (with decomposition).

Provenance & Evidence