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

HRID 1703580Notes

Reaction equation

HRID 1703580 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH2:14]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:15][CH2:16][CH3:17]>C(=S)=S>[CH2:14]([C:18]1[CH:23]=[CH:22][C:21]([C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:8])=[CH:20][CH:19]=1)[CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 7705ButylbenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 14148735(4-Butylphenyl)(phenyl)methanoneYield 96.8%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

A 2.8 g (0.02 mole) of benzoic acid chloride was dissolved in 30 ml of carbon disulfide and then, 4.0 g (0.03 mole) of anhydrous aluminum chloride was added to the solution. A 2.68 g (0.02 mole) of n-butyl benzene was further added to the mixture with stirring, and the reaction was carried out at room temperature for 18 hours. Carbon disulfide was distilled off from the reaction mixture and water was added and the reaction product was extracted with benzene. The benzene phase was separated and washed with 1N-NaOH and with water and was dried with anhydrous sodium sulfate. The solvent was distilled off to obtain a pale yellow oily product. The oily product was distilled under a reduced pressure to obtain 4.6 g of 4-n-butyl benzophenone having a boiling point of 184° to 188° C./6 mmHg. (yield of 96.8%).

Workup

  1. distillationCarbon disulfide was distilled off from the reaction mixture and water
  2. additionwas added
  3. extractionthe reaction product was extracted with benzene
  4. customThe benzene phase was separated
  5. washwashed with 1N-NaOH and with water
  6. dry with materialwas dried with anhydrous sodium sulfate
  7. distillationThe solvent was distilled off
  8. customto obtain a pale yellow oily product
  9. distillationThe oily product was distilled under a reduced pressure

Sources & evidence

ORD record
ord-ae7dc010e42c41988dc9d88c23ae4f11
Source dataset
uspto-grants-1978_11
Patent number
US04124726

Reaction notes

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