3,5-Dimethylbenzoyl Chloride → 4-Chloro-3',5'-dimethylbenzophenone

HRID 2174413Notes

Reaction equation

HRID 2174413 reaction equation
[Cl-:1].[Cl-].[Cl-].[Al+3].[CH3:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([CH3:15])[CH:14]=1)[C:9](Cl)=[O:10]>ClC1C=CC=CC=1>[CH3:5][C:6]1[CH:7]=[C:8]([C:9](=[O:10])[C:6]2[CH:7]=[CH:8][C:12]([Cl:1])=[CH:13][CH:14]=2)[CH:12]=[C:13]([CH3:15])[CH:14]=1

Participants

4

Reactant 2

HCID 810883,5-Dimethylbenzoyl ChlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 27574834-Chloro-3',5'-dimethylbenzophenoneYield 172.3%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
70 °C

Procedure

100 ml chlorobenzene and 14.7 g aluminium trichloride are added in a 250 ml three-neck flask, and then 16.8 g 3,5-dimethyl benzoyl chloride is dropped into the solution at room temperature. Maintaining the temperature at 70° C., react with stirring for 16 h. The reaction solution is acidolyzed and washed with water, and then is distilled to remove chlorobenzene, obtaining 21 g residue, the yield is 86%. The residue is recrystallized with ethanol to obtain a purified white crystal, and the melting point is 72-73° C. 1H-NMR data (solvent CDCl3): δ2.371 ppm, s, 6H, δ7.230 ppm, s, 1H, δ7.363 ppm, s, 2H; δ7.438, 7.466 ppm, d, 2H, δ7.729, 7.757 ppm, d, 2H.

Workup

  1. customreact
  2. washwashed with water
  3. distillationis distilled
  4. customto remove chlorobenzene

Sources & evidence

ORD record
ord-9b82f82c19844808a946464e3fade4bc
Source dataset
uspto-grants-2015_06
Patent number
US09061979B2

Reaction notes

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