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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1277716Generated: November 4, 2026

4-Chlorophenol → 9,10-Anthracenedione, 1-amino-2-(4-chlorophenoxy)-4-hydroxy-

https://huagongshe.com/reaction/1277716

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-ChlorophenolHCID 4684—
ReactantSodium CarbonateHCID 10340—
ReactantPotassium CarbonateHCID 11430—
Reactant9,10-Anthracenedione, 1-amino-2-chloro-4-hydroxy-HCID 75590—
Reactantdodecylbenzenesulphonic acid, compound with 2,2'-iminodiethanol (1:1)HCID 57371087—
CatalystBenzyltrimethylammonium chlorideHCID 5963—
SolventWaterHCID 962—
Product9,10-Anthracenedione, 1-amino-2-(4-chlorophenoxy)-4-hydroxy-HCID 17071697%

Reaction Conditions

Temperature140 °C

Reaction Steps

35 parts of potassium carbonate, 65 parts of p-chlorophenol, 4 parts of a 50% strength aqueous solution of diethanolamine dodecylbenzenesulfonate to act as a dispersant, 7 parts of a 50% strength aqueous solution of trimethylbenzylammonium chloride and 70 parts of 1-amino-2-chloro-4-hydroxyanthraquinone (95% pure) are introduced into 250 parts of water (resulting in a pH of 11), and the mixture is heated for 15 hours at 140° C., under a pressure of about 4.5 bar, whilst stirring. When it has cooled, the reaction mixture is poured into 350 parts of 10% strength sodium carbonate solution and the suspension is stirred for 1 hour at 70° C. and then filtered. The product is washed neutral and dried, giving 88 parts of 97% pure 1-amino-2-(4'-chlorophenoxy)-4-hydroxyanthraquinone, corresponding to a yield of 97% of theory.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04278606
Source datasetuspto-grants-1981_07
ORD IDord-f99bb4c15efd4c2fbb1395d337e115e0
Source noteuspto-grants-1981_07