Mesitylene → Methanone, (4-chlorophenyl)(2,4,6-trimethylphenyl)-

HRID 280672Notes

Reaction equation

HRID 280672 reaction equation
[C:1]1([CH3:9])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[CH:2]=1.[Cl:10][C:11]1[CH:19]=[CH:18][C:14]([C:15](Cl)=[O:16])=[CH:13][CH:12]=1.[Cl-].[Al+3].[Cl-].[Cl-]>C(=S)=S>[Cl:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([C:2]2[C:3]([CH3:8])=[CH:4][C:5]([CH3:7])=[CH:6][C:1]=2[CH3:9])=[O:16])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7947MesityleneHCID 85014-Chlorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 11108032Methanone, (4-chlorophenyl)(2,4,6-trimethylphenyl)-Yield 62%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Conditions

Temperature
0 °C

Procedure

A stirred 0° C. solution of mesitylene (7.21 g, 60.0 mmol) and 4-chlorobenzoyl chloride (10.55 g, 60.0 mmol) in carbon disulfide (130 ml) was treated with aluminum chloride (8.83 g, 66.1 mmol) in portions over 10 minutes. The mixture was stirred 75 minutes at 0° C., warmed to ambient temperature over 30 minutes, refluxed 10 hours, kept at ambient temperature 6 hours, cooled to 0° C., and quenched by addition of ice (250 g) and concentrated hydrochloric acid (50 ml). The mixture was extracted twice with diethyl ether and the combined extracts were washed with water (3X), saturated aqueous sodium carbonate, and brine, dried over anhydrous magnesium sulfate, and evaporated to dryness at 30° C. under vacuum. The residue was crystallized from methanol and dried to provide 9.61 g (62%) 4-chlorobenzoylmesitylene, m.p. 65.5°-66.5° C.

Workup

  1. temperaturewarmed to ambient temperature over 30 minutes
  2. temperaturerefluxed 10 hours
  3. waitkept at ambient temperature 6 hours
  4. temperaturecooled to 0° C.
  5. customquenched by addition of ice (250 g) and concentrated hydrochloric acid (50 ml)
  6. extractionThe mixture was extracted twice with diethyl ether
  7. washthe combined extracts were washed with water (3X), saturated aqueous sodium carbonate, and brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customevaporated to dryness at 30° C. under vacuum
  10. customThe residue was crystallized from methanol
  11. customdried

Sources & evidence

ORD record
ord-0787197a1b4649f3bb593f65a2d6d6a1
Source dataset
uspto-grants-1986_05
Patent number
US04590201

Reaction notes

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