Methanol → n,n'-bis(4-hydroxyphenyl)benzene-1,4-dicarboxamide

Participants

Reaction Conditions

Reaction Steps

N,N'-bis(4-hydroxyphenyl)terephthalamide (Structure V) was synthesized by the reaction of aminophenol with terephthaloyl chloride in the presence of NaHCO3. Two moles of aminophenol (218.3 grams) and 2 moles of NaHCO3 (168 grams) were first added to a stirred, round bottom flask containing 750 milliliters of acetone and 750 milliliters of deionized water. Two moles of terephthaloyl chloride (203.0 grams) were then added over a two hour period. During the course of the terephthaloyl chloride addition, 200 additional milliliters of acetone were also added to wash down the frothy suspension caused by CO2 evolution. After the terephthaloyl chloride addition, the precipitate produced from the reaction was collected by vacuum filtration. For purification of the precipitate obtained, one half of this material was placed in a stirred, round bottom flask containing 900 milliliters of methanol and 450 milliliters of deionized water. This suspension was heated to 56° C. and then vacuum filtered. For the solids recovered from this filtration, the washing step with methanol and deionized water was repeated. The filtrant solids obtained from the second hot filtration were then added to a stirred, round bottom flask containing 1250 milliliters of methanol. This suspension was vacuum filtered after 30 minutes to recover the solids for drying. After following the preceding washing procedure for the second half of the reaction precipitate, the total solids recovered were dried at 80° C. under vacuum for 5 hours. The weight of the dried solids was 325.6 grams, 93.4 percent of the theoretical yield to N,N'-bis(4-hydroxyphenyl)terephthalamide. The melting point of this final product was 405° C. as determined by DSC. ##STR13##

Provenance & Evidence