Benzene → 3-Chlorobenzophenone

HRID 47002

Reaction equation

HRID 47002 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].[CH:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Cl-].[Al+3].[Cl-].[Cl-]>CCOCC>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:6]

Participants

5

Reactant 3

HCID 241BenzeneHCID 69252Benzoyl chloride, 3-chloro-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 660983-Chlorobenzophenone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a refluxing solution containing 43.9 g (0.25 mole) of 3-chlorobenzoyl chloride in 120 ml. of dry benzene is added 30.0 g. (0.225 mole) of anhydrous aluminum chloride in several portions over a period of 10 minutes. When the reaction is complete, as indicated by vapor phase chromatographic (vpc) techniques, the mixture is cooled to 25° and diluted with ether. Extraction with dilute base is followed by thorough drying (magnesium sulfate) and concentration in vacuo. Final purification is effected by recrystallization from ether-hexane to afford 13.7 g (0.06 mole) of 3-chlorobenzophenone, m.p. 84°14 85°.

Workup

  1. temperaturethe mixture is cooled to 25°
  2. extractionExtraction
  3. additionwith dilute base
  4. customby thorough drying
  5. concentration(magnesium sulfate) and concentration in vacuo
  6. customFinal purification
  7. customis effected by recrystallization from ether-hexane

Sources & evidence

ORD record
ord-15a97d0c27f449c78d07e3ae923f3116
Source dataset
uspto-grants-1979_11
Patent number
US04175945

Linked notes

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