2,6-Dichlorobenzoyl chloride → (2,6-Dichlorophenyl)(4-methylphenyl)methanone

HRID 280668Notes

Reaction equation

HRID 280668 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4](Cl)=[O:5].[Cl-].[Al+3].[Cl-].[Cl-]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4]([C:9]1[CH:8]=[CH:7][C:3]([CH3:4])=[CH:2][CH:10]=1)=[O:5]

Participants

4

Reactant 2

HCID 783922,6-Dichlorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 13649652(2,6-Dichlorophenyl)(4-methylphenyl)methanoneYield 115.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

An 80° C., stirred solution of 2,6-dichlorobenzoyl chloride (17.3 g, 82.6 mmol) in toluene (30 ml) was treated in portions with aluminum chloride (11.0 g, 82.3 mmol). After 12 hours at 80° C., the mixture was cooled, quenched with ice water and concentrated hydrochloric acid (10 ml), and separated. The aqueous phase was extracted with diethyl ether (2×150 ml) and the combined organic phases were washed twice with water, dried over anhydrous magnesium sulfate, and evaporated to dryness under vacuum. The residue was crystallized from hexane to provide 12.6 g (58%) 4-(2,6-dichlorobenzoyl)toluene, m.p. 109°-111.5° C.

Workup

  1. temperaturethe mixture was cooled
  2. customquenched with ice water and concentrated hydrochloric acid (10 ml)
  3. customseparated
  4. extractionThe aqueous phase was extracted with diethyl ether (2×150 ml)
  5. washthe combined organic phases were washed twice with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated to dryness under vacuum
  8. customThe residue was crystallized from hexane

Sources & evidence

ORD record
ord-3181757ca6674ad49f85059cf5121de7
Source dataset
uspto-grants-1986_05
Patent number
US04590201

Reaction notes

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