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

HRID 1277716Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.C(OS(C1C=CC=CC=1)(=O)=O)CCCCCCCCCCC.N(CCO)CCO.[NH2:44][C:45]1[C:58]2[C:57](=[O:59])[C:56]3[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=3)[C:50](=[O:60])[C:49]=2[C:48]([OH:61])=[CH:47][C:46]=1Cl.C(=O)([O-])[O-].[Na+].[Na+]>[Cl-].C[N+](C)(C)CC1C=CC=CC=1.O>[NH2:44][C:45]1[C:58]2[C:57](=[O:59])[C:56]3[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=3)[C:50](=[O:60])[C:49]=2[C:48]([OH:61])=[CH:47][C:46]=1[O:14][C:11]1[CH:12]=[CH:13][C:8]([Cl:7])=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 140 °C

Procedure

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.

Workup

customresulting in a pH of 11), and the mixture
temperatureWhen it has cooled
stirringthe suspension is stirred for 1 hour at 70° C.
filtrationfiltered
washThe product is washed neutral
customdried

Sources & evidence

ORD record: ord-f99bb4c15efd4c2fbb1395d337e115e0
Source dataset: uspto-grants-1981_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04278606

Reaction notes

Loading…