Benzene → 1,4-Dibenzoylbenzene

HRID 462373Notes

Reaction equation

HRID 462373 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:15])[C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][CH:7]=1.O.[CH:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[C:5]([C:6]1[CH:14]=[CH:13][C:9]([C:10](=[O:11])[C:6]2[CH:14]=[CH:13][CH:9]=[CH:8][CH:7]=2)=[CH:8][CH:7]=1)(=[O:15])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 4

HCID 241Benzene2×HCID 962WaterHCID 7488Terephthaloyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 763951,4-Dibenzoylbenzene

Procedure

To a stirred slurry of 50 g of aluminium chloride in 150 ml of benzene under reflux was added dropwise 40 g of terephthaloyl chloride dissolved in 250 ml of benzene. When the addition was complete the reaction was refluxed for 15 minutes, and 250 ml of water was added slowly. The benzene layer was separated and the aqueous layer was extracted with methylene chloride (2×300 ml). The combined orgainic layers were washed with 1m NaOH solution (2×400 ml) and water (400 ml), dried (MgSO4), filtered, and the solvents were removed under reduced pressure to give a nearly colorless solid. Recrystallization from 95% ethanol gave 46.8 g of colorless 1,4-dibenzoylbenzene, m.p. 160°-162°.

Workup

  1. additionWhen the addition
  2. temperaturewas refluxed for 15 minutes
  3. customThe benzene layer was separated
  4. extractionthe aqueous layer was extracted with methylene chloride (2×300 ml)
  5. washThe combined orgainic layers were washed with 1m NaOH solution (2×400 ml) and water (400 ml)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvents were removed under reduced pressure
  9. customto give a nearly colorless solid
  10. customRecrystallization from 95% ethanol

Sources & evidence

ORD record
ord-40608849773846f9b7dcef11fb1e24a0
Source dataset
uspto-grants-1985_05
Patent number
US04515666

Reaction notes

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