4-Chloro-9,10-dioxo-9,10-dihydroanthracene-1-carboxylic acid → 1-Chloroanthraquinone

HRID 1284149Notes

Reaction equation

HRID 1284149 reaction equation
[Cl: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](C(O)=O)=[CH:4][CH:3]=1>[Cu-]=O.CN(C)C=O>[Cl: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[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 2355754-Chloro-9,10-dioxo-9,10-dihydroanthracene-1-carboxylic acid

Product 1

HCID 67091-ChloroanthraquinoneYield 83.4%

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 20 parts of 4-chloroanthraquinone-1-carboxylic acid, 200 parts of dimethylformamide and 3 parts of copper (I) oxide is heated for four hours at 150°C. The end product is precipitated by pouring the mixture into 400 parts of water and filtered. 14 parts (83.4% of theory) of 1-chloroanthraquinone is obtained having a melting point of 154° to 157°C.

Workup

  1. customThe end product is precipitated
  2. additionby pouring the mixture into 400 parts of water
  3. filtrationfiltered

Sources & evidence

ORD record
ord-ebc1ac81b6a2445c918ad8dbbb6a3649
Source dataset
uspto-grants-1976_08
Patent number
US03978096

Reaction notes

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