Reaction #5663

Reaction equation

bis(3,4-diaminophenyl)ether

phenyl-4-hydroxybenzoate

diphenylsulfone

toluene

→

tan solid

Yield 30.0%

5,5'-Oxy-bis[2-(4-hydroxyphenyl)benzimidazole]

Yield 30.0%

Conditions

Workup

1. 1
   OtherThe toluene was removed
2. 2
   Temperaturethe temperature increased to 250° C.
3. 3
   Temperaturemaintained for 1.5 hours
4. 4
   Temperaturethe temperature increased to 280° C.
5. 5
   Temperaturemaintained for 1.25 hours
6. 6
   OtherThe cooled dark reaction mixture
7. 7
   Washwas washed in hot toluene
8. 8
   Otherdried at 110° C.
9. 9
   Otherto afford 20.59 g (50% crude yield) of a dark purple powder
10. 10
    ExtractionThe dark solid was extracted with acetone

Procedure

A mixture of bis(3,4-diaminophenyl)ether (22.00 g, 0.096 mol), phenyl-4-hydroxybenzoate (41.00 g, 0.194 mol), diphenylsulfone (110.17 g), and toluene (135 ml) was heated under a nitrogen atmosphere for 3.5 hours at 150° C. The toluene was removed and the temperature increased to 250° C. and maintained for 1.5 hours. A vacuum was subsequently applied and the temperature increased to 280° C. and maintained for 1.25 hours. The cooled dark reaction mixture was washed in hot toluene and dried at 110° C. to afford 20.59 g (50% crude yield) of a dark purple powder. The dark solid was extracted with acetone to afford 12.39 g (30% yield) of a tan solid. The endothermic peak as determined by DTA was 317° C. (broad). Analysis calcd. for C26H18N4O3 : C, 71.88%; H, 4.18%; N, 12.90%. Found: C, 71.91%; H, 4.22%; N, 13.06%. The resulting monomer had the following structural formula: ##STR11##

Source