Toluene → (1,4-Phenylene)bis[(4-methylphenyl)methanone]

HRID 462374Notes

Reaction equation

HRID 462374 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-].[C:17]1([CH3:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH3:23][C:17]1[CH:22]=[CH:21][C:20]([C:1]([C:2]2[CH:10]=[CH:9][C:5]([C:6](=[O:7])[C:5]3[CH:9]=[CH:10][C:2]([CH3:1])=[CH:3][CH:4]=3)=[CH:4][CH:3]=2)=[O:11])=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 7488Terephthaloyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 254455(1,4-Phenylene)bis[(4-methylphenyl)methanone]

Procedure

To a stirred mixture of 40 g of terephthaloyl chloride and 200 ml of toluene was added in portions 56 g of solid aluminium chloride at such a rate to maintain the reaction temperature at 45°-55°. The thick orange slurry was then heated to 75° for 2 hours, cooled in ice and slowly treated with 200 ml of dilute HCL. The slurry was stirred for 2 hours at room temperature. The solid was collected by filtration, washed with 200 ml of petroleum ether and 2 L of hot water, and dried to constant weight to give 51 g of colorless product, m.p. 178°-187°. This material was used without further purification.

Workup

  1. temperatureto maintain the reaction temperature at 45°-55°
  2. temperatureThe thick orange slurry was then heated to 75° for 2 hours
  3. temperaturecooled in ice
  4. additionslowly treated with 200 ml of dilute HCL
  5. filtrationThe solid was collected by filtration
  6. washwashed with 200 ml of petroleum ether and 2 L of hot water
  7. customdried to constant weight

Sources & evidence

ORD record
ord-b6d31b31ce05447586b30299c6c12065
Source dataset
uspto-grants-1985_05
Patent number
US04515666

Reaction notes

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