Benzene → Anthraquinone

HRID 649273Notes

Reaction equation

HRID 649273 reaction equation
[CH:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Al+3].[Cl-].[Cl-].[Cl-].[C:11](Cl)(=[O:21])[C:12]1[C:13](=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:14](Cl)=[O:15].C(O)(=O)C(O)=O>[N+](C1C=CC=CC=1)([O-])=O.CCO>[CH:1]1[C:6]2[C:14](=[O:15])[C:13]3[C:12](=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:11](=[O:21])[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 241BenzeneHCID 971Oxalic AcidHCID 6955Phthaloyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 6780AnthraquinoneYield 85%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 7416NitrobenzeneSolvent3×

Conditions

Temperature
100 °C

Procedure

7.2 g (0.2 mols) of benzene were added at ambient temperature and in a gentle stream of dry nitrogen to 26.6 g (0.2 mols) of anhydrous AlCl3 in 300 ml nitrobenzene. The mixture was heated to 100° C.; after agitation for 15 minutes at this temperature, 20.2 g (0.1 mols) of phthalic acid dichloride dissolved in 100 ml nitrobenzene were added during about 20 minutes. The volume of the solution was made up to 500 ml with nitrobenzene and the temperature was kept at 100° C. with agitation for 30 minutes, after which the reacting substance was cooled and 300 ml of saturated aqueous solution of oxalic acid was added with intense agitation. Three extractions were made, each time with 200 ml ethyl ether and the combined extracts were dried over anhydrous Na2SO4. The solvent was removed under reduced pressure and the product was purified by crystallization from toluene, giving 17.7 g (85% yield) of 9,10-anthraquinone (1), m.p. 285° C. (literature: 286° C., EtOH).

Workup

  1. additionwere added during about 20 minutes
  2. temperatureafter which the reacting substance was cooled
  3. extractionThree extractions
  4. dry with materialeach time with 200 ml ethyl ether and the combined extracts were dried over anhydrous Na2SO4
  5. customThe solvent was removed under reduced pressure
  6. customthe product was purified by crystallization from toluene

Sources & evidence

ORD record
ord-7189f74b51c8434884da558c1e569206
Source dataset
uspto-grants-1988_04
Patent number
US04739062

Reaction notes

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