Quinizarin → 1,4,9,10-Anthradiquinone

HRID 2397267

Reaction equation

HRID 2397267 reaction equation
[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:17])[C:6]=2[C:5]([OH:18])=[CH:4][CH:3]=1.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4]>C(O)(=O)C>[C:2]1(=[O: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](=[O:18])[CH:4]=[CH:3]1

Participants

4

Reactant 2

HCID 6688QuinizarinHCID 178418268HCID 178418268, compound

Product 1

HCID 1371691,4,9,10-AnthradiquinoneYield 82.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1,4-dihydroxyanthraquinone (10.0 g), lead tetraacetate (20 g) and acetic acid (25 ml) was ground together in mortar and pestle for 10 minutes at 25°. The reaction mixture was filtered and the solid washed with acetic acid, water, and ether. The red solid was taken up in a large volume of aceton (700 ml), the solution filtered through Celite, dried over sodium sulfate and evaporated under reduced pressure to give 1,4,9,10 anthradiquinone (8.2 g, 81% yield) as a brown solid. m.p. 213°-215° C. (benzene/pet. ether) lit m.p. 211°-213° NMR (CDCl3) δ8.2-7.8 (m, 4H aryl), 6.88 (s, 2H); IR 5.95, 610 (sh), 6.15 (sh), 6.3μ.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe solid washed with acetic acid, water, and ether
  3. filtrationthe solution filtered through Celite
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-fb0ebff14f294ab8bc22ff31b17d8c84
Source dataset
uspto-grants-1977_05
Patent number
US04021457

Linked notes

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