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

HRID 1980083Notes

Reaction equation

HRID 1980083 reaction equation
[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5]([OH:18])=[CH:4][C:3]=1[Cl:19].ClC1C=CC=CC=1.[C:27]1([OH:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[OH-].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5]([OH:18])=[CH:4][C:3]=1[Cl:19].[C:27]1([O-:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

8

Reactant 4

HCID 996PhenolHCID 7964ChlorobenzeneHCID 14797Potassium HydroxideHCID 755909,10-Anthracenedione, 1-amino-2-chloro-4-hydroxy-

Product 2

HCID 755909,10-Anthracenedione, 1-amino-2-chloro-4-hydroxy-HCID 119047Phenolate

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

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.

Workup

  1. customtemperature (131°-133° C.)
  2. stirringstirred for 5 hours at the boiling temperature
  3. distillationis distilled off at the side, together with about 10 ml of chlorobenzene
  4. addition50 ml of methanol are added
  5. filtrationthe precipitate is filtered off
  6. washwashed with methanol and water
  7. customdried

Sources & evidence

ORD record
ord-a8dfe8be438048169a567302b74823a9
Source dataset
uspto-grants-1984_11
Patent number
US04485043

Reaction notes

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