1,2,3-Trichlorobenzene → 1,2,3-Trichlorobenzene

HRID 258940

Reaction equation

HRID 258940 reaction equation
OS(O)(=O)=O.O=S(=O)=O.[C:10]([C:14]1[C:15]([C:23](=[O:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17](O)=[O:18])([CH3:13])([CH3:12])[CH3:11].[Cl:31][C:32]1[C:33]([Cl:39])=[C:34]([Cl:38])[CH:35]=[CH:36][CH:37]=1>O>[Cl:31][C:32]1[C:33]([Cl:39])=[C:34]([Cl:38])[CH:35]=[CH:36][CH:37]=1.[C:10]([C:14]1[C:15]2[C:23](=[O:30])[C:24]3[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:17](=[O:18])[C:16]=2[CH:20]=[CH:21][CH:22]=1)([CH3:13])([CH3:11])[CH3:12]

Participants

6

Reactant 3

HCID 68951,2,3-TrichlorobenzeneHCID 24681Fuming sulfuric acid2×HCID 86734930Tertiary butylbenzoylbenzoic acid

Product 2

HCID 68951,2,3-TrichlorobenzeneHCID 142749441-tert-Butylanthracene-9,10-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To 400 parts of 10.5% oleum there was added a solution of 100 parts of tertiary butylbenzoylbenzoic acid in 600 parts of commercial trichlorobenzene. The solution was added gradually over a 30 minute period to the well-stirred oleum held at 80° to 90° C. After the addition was complete, the reaction mixture was stirred at 90° C for 4 hours, then poured into 2000 parts of cold water. The aqueous and organic layers were allowed to separate, and the aqueous layer was removed by decantation. After washing the organic layer twice with 800 part portions of water, the residual acidity was neutralized by stirring the organic layer with another 800 parts of water, sufficient 30% aqueous sodium hydroxide solution being added to achieve a pH above 7.0. A final 800 part water wash was applied, and the product was fractionally distilled. From 562 parts of crude product there was obtained 480 parts of trichlorobenzene, 80 parts of tertiary butylanthraquinone-containing product and 6 parts of residual high-boiling tar. The product was 98.4 % tertiary butylanthraquinone. The yield was 86% of theory.

Workup

  1. customheld at 80° to 90° C
  2. additionAfter the addition
  3. customto separate
  4. customthe aqueous layer was removed by decantation
  5. washAfter washing the organic layer twice with 800 part portions of water
  6. stirringby stirring the organic layer with another 800 parts of water, sufficient 30% aqueous sodium hydroxide solution
  7. additionbeing added
  8. washA final 800 part water wash
  9. distillationthe product was fractionally distilled

Sources & evidence

ORD record
ord-8a6ee73fad0f44f4b929b2314940ac52
Source dataset
uspto-grants-1977_07
Patent number
US04035396

Linked notes

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