4-Chlorophenol → Quinizarin

HRID 236676

Reaction equation

HRID 236676 reaction equation
[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9](O)[CH:10]=[CH:11][C:12]=3O)[C:7](=[O:19])[C:6]=2[C:5]([OH:20])=[CH:4][CH:3]=1.C1(=O)OC(=O)C2=CC=CC=C12.ClC1C=CC(O)=CC=1>OS(O)(=O)=O.O=S(=O)=O.[B]>[OH: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:19])[C:6]=2[C:5]([OH:20])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 46844-ChlorophenolHCID 66861,4,5,8-Tetrahydroxy-9,10-anthracenedioneHCID 6811Phthalic Anhydride

Product 1

HCID 6688Quinizarin

Reagents, catalysts & solvents 2

HCID 5462311BoronCatalystHCID 24681Fuming sulfuric acidSolvent

Procedure

The present invention relates to a process for the production of 1,4,5,8-tetrahydroxyanthraquinone (hereinafter referred to as diquinizarine) by reacting phthalic anhydride with p-chlorophenol in oleum and in the presence of boron catalysts to give the boron complex of 1,4-dihydroxyanthraquinone, and then chlorinating this boron complex direct with chlorinating agents, in the same reaction medium, to give the boron complex of 5,8-dichloro-1,4-dihydroxyanthraquinone, and subsequently hydrolysing this chlorinated boron complex to diquinizarine.

Sources & evidence

ORD record
ord-7730aea525044608bb2f78f4cd3c1841
Source dataset
uspto-grants-1987_02
Patent number
US04645626

Linked notes

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