2-[2-[2-(2-hydroxyphenoxy)ethoxy]ethoxy]phenol

Conditions: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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). 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 dried in vacuo at 70° C

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A vigorously agitated mixture of 220 grams (2 gram-mols) of catechol, 2000 ml. of water, 80 grams (2 gram-mols) of sodium hydroxide and 143 grams (1 grammol) of bis(beta-chloroethyl)ether is reacted at reflux at 102°-103°C. for 16 hours under nitrogen. It is then acidified with concentrated hydrochloric acid. When unreacted bis(2-chloroethyl)ether and 1000 ml. of water have been removed by distillation, the mixture separates into two layers. The organic layer is recovered and treated with 700 ml. of methanol and chilled with ice water. The crystals that subsequently form are filtered off, washed with cold methanol, and dried. The 2,2'-(oxydiethylenedioxy)-diphenol product, 67 to 74 grams (23 to 25.5% yield), melts at 85°C. and analyzes as follows (a typical example. at reflux at 102°-103°C. for 16 hours under nitrogen of water have been removed by distillation The organic layer is recovered treated with 700 ml of methanol and chilled with ice water The crystals that subsequently form are filtered off washed with cold methanol dried

Conditions: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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). 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 dried in vacuo at 70° C