Hydrochloric Acid → 1,4-Naphthalenedicarboxylic acid

Participants

Reaction Steps

125.6 parts by weight of 4-bromo-1-naphthoic acid with a melting point of 219°-220° and 51 parts by weight of copper-(I) cyanide (67-71% copper) are introduced into 330 parts by weight of dimethylformamide. The mixture is then heated under reflux for 4 hours, whilst stirring, to 150°-160° C., whereby, after some time, the solid materials go into solution, but then the 4-cyano-1-naphthoic acid copper bromide complex is gradually precipitated. After cooling to about 100°, the reaction mixture is diluted with 330 parts by weight of water and stirred for approximately one hour at room temperature, and the precipitate is filtered off by suction and rinsed with about 400 parts by weight of water. The 4-cyanonaphthoic acid/copper bromide complex thus isolated is introduced into 550 parts by weight of 20% sodium hydroxide solution and heated under reflux for 5 hours. The mixture is then adjusted to pH 7.0-7.5 with about 220 parts by weight of concentrated hydrochloric acid, the solution is filtered off by suction from the copper oxide slurry deposited and this slurry is rinsed with about 500 parts by weight of water, in portions. The naphthalene-1,4-dicarboxylic acid is precipitated from the filtrate at pH 2 by the addition of about 100 parts by weight of concentrated hydrochloric acid, and the precipitate is filtered off under suction and is washed with water until free of chloride ions. After drying, 92 parts by weight of a practically colorless naphthalene-1,4-dicarboxylic acid with a melting point of 315°-320° are obtained.

Provenance & Evidence