Phenol → 9,10-Anthracenedione, 1-amino-2-chloro-4-hydroxy-

Participants

Reaction Conditions

Reaction Steps

29.75 g of 1-amino-2-chloro-4-hydroxyanthraquinone (titer 92%), 120 ml of chlorobenzene, 5 g of tetrabutylammonium bromide, 10.8 g of phenol and 6.48 g of potassium hydroxide are heated within 1 hour, with stirring, to boiling temperature (131°-133° C.), and then stirred for 5 hours at the boiling temperature. Reaction water occurring during the process is distilled off at the side, together with about 10 ml of chlorobenzene. The reaction mixture is subsequently cooled to 60° C., and 50 ml of methanol are added; the precipitate is filtered off, washed with methanol and water and then dried. The yield is 29.9 g of 1-amino-4-hydroxy-2-phenoxyanthraquinone (90.3% of theory). The product dyes polyester in exactly the same manner as the commercial product does, produced from 1-amino-2-chloro-4-hydroxyanthraquinone in phenol in the presence of phenolate.

Provenance & Evidence