4-Chlorobenzoyl chloride → HCID 20496044, compound

HRID 461518Notes

Reaction equation

HRID 461518 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH2:5]([CH2:12][C:13](=[O:15])[CH3:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Cl:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1>C(=S)=S>[Cl:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([C:9]2[CH:10]=[CH:11][C:6]([CH2:5][CH2:12][C:13](=[O:15])[CH3:14])=[CH:7][CH:8]=2)=[O:22])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 17355Benzyl acetoneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 20496044HCID 20496044, compound

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a vigorously stirred solution of aluminium chloride (0.2 mole) in carbon disulphide (200 ml.) at 0° C was added a mixture of benzylacetone (0.1 mole) and p-chlorobenzoyl chloride (0.1 mole) throughout 20 minutes. After a further hour at 0° C, the reaction was allowed to reach room temperature and left overnight. The supernatant carbon disulphide was decanted off and the crude, brown residual oil, was poured carefully onto a mixture of ice and concentrated hydrochloric acid. Work-up in the usual way afforded an oil, which, after trituration with acetone and re-crystallisation from benzene/60°-80° C petrol, gave pure 4-[4-(p-chlorobenzoyl)phenyl]-2-butanone as colourless needles, m.pt. 91° - 2° C.

Workup

  1. waitAfter a further hour at 0° C
  2. customto reach room temperature
  3. customThe supernatant carbon disulphide was decanted off
  4. additionthe crude, brown residual oil, was poured carefully onto a mixture of ice and concentrated hydrochloric acid
  5. customafforded an oil, which
  6. customafter trituration with acetone and re-crystallisation from benzene/60°-80° C petrol

Sources & evidence

ORD record
ord-d5758a0c165c448fb6ae8b683d3bb385
Source dataset
uspto-grants-1977_12
Patent number
US04062978

Reaction notes

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