Benzoyl chloride → (4-Cyclohexylphenyl)(phenyl)methanone

HRID 1732629Notes

Reaction equation

HRID 1732629 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH:5]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)Cl>[CH:11]1([C:5]2[CH:6]=[CH:7][C:8]([C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:24])=[CH:9][CH:10]=2)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 13229CyclohexylbenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 265880(4-Cyclohexylphenyl)(phenyl)methanoneYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

67 g (0.5 mol) of aluminium chloride are added in portions to a mixture of 80 g (0.5 mol) of cyclohexylbenzene 70 g (0.5 mol) of benzoyl chloride and 500 ml of methylene chloride at room temperature. After 15 hours, the reaction mixture is poured onto ice/hydrochloric acid. The organic phase is washed with water until neutral, dried over sodium sulphate and evaporated. The crude product is purified by distillation. 93.3 g (75% of theory) of 4-cyclohexylbenzophenone of boiling point 160° to 175° C./0.1 mm are obtained.

Workup

  1. additionthe reaction mixture is poured onto ice/hydrochloric acid
  2. washThe organic phase is washed with water until neutral,
  3. dry with materialdried over sodium sulphate
  4. customevaporated
  5. distillationThe crude product is purified by distillation

Sources & evidence

ORD record
ord-8f91a212420449fbb3fffc75dd7d4e02
Source dataset
uspto-grants-1980_12
Patent number
US04238498

Reaction notes

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