Benzene → 1,4-Dibenzoylbenzene

HRID 442249Notes

Reaction equation

HRID 442249 reaction equation
[C:1](Cl)(=[O:11])[C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl.[CH:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[C:1]([C:2]1[CH:10]=[CH:9][C:5]([C:6](=[O:7])[C:2]2[CH:10]=[CH:9][CH:5]=[CH:4][CH:3]=2)=[CH:4][CH:3]=1)(=[O:11])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 4

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 7488Terephthaloyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 763951,4-Dibenzoylbenzene

Procedure

1,4-Dibenzoylbenzene is prepared essentially as described by Noelting and Kohn, Ber. 19, 147 (1886). Terephthaloyl dichloride (20.3 g, 0.1 mole) is dissolved in benzene (350 ml) and anhydrous aluminum chloride (30 g, 0.22 mole) is added. The mixture is heated at 70° for 7 hours, cooled to 20° and maintained at this temperature for eighteen hours with continual stirring. The reaction mixture is then added to 1 l crushed ice and 20 ml 37% hydrochloric acid. The benzene solution is washed three times with water and twice with sodium bicarbonate solution. The excess benzene is removed by distillation. The resulting crystalline material is recrystallized from dimethylformamide, yield 22 g (76% of theory) white crystals mp 158°-159°.

Workup

  1. temperatureThe mixture is heated at 70° for 7 hours
  2. temperaturecooled to 20°
  3. temperaturemaintained at this temperature for eighteen hours with continual stirring
  4. additionThe reaction mixture is then added to 1 l
  5. washThe benzene solution is washed three times with water
  6. customThe excess benzene is removed by distillation
  7. customThe resulting crystalline material is recrystallized from dimethylformamide, yield 22 g (76% of theory) white crystals mp 158°-159°

Sources & evidence

ORD record
ord-36187af6e739466a8b5d200ebafdb1bc
Source dataset
uspto-grants-1977_08
Patent number
US04044139

Reaction notes

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