Synthesis
General procedure for the synthesis of 2,2'-diaminodiphenyl ether from 2,2'-oxo-bis(nitrobenzene): first, an aqueous suspension of iron powder and hydrochloric acid was refluxed under stirring for 25 minutes. Subsequently, the corresponding dinitro compound was added to this hot suspension and the reflux reaction was continued for 24 hours. Upon completion of the reaction, the mixture was cooled to room temperature and hydrolyzed with 20 mL of 2.5 M sodium hydroxide solution. Next, the reaction mixture was extracted with chloroform (20 mL each time, twice). The organic phases were combined, dried with anhydrous sodium sulfate and finally the solvent was evaporated to give the target product 2,2'-diaminodiphenyl ether as a solid.
References
[1] Tetrahedron, 1995, vol. 51, # 2, p. 579 - 590
[2] Polyhedron, 2015, vol. 90, p. 165 - 174
[3] Synthesis, 1996, # 8, p. 930 - 940
[4] Journal of Organic Chemistry, 1994, vol. 59, # 24, p. 7306 - 7315
[5] Zeitschrift fur Anorganische und Allgemeine Chemie, 2015, vol. 641, # 1, p. 128 - 135
