Aluminum(III) Chloride → 4-(4-Chlorobenzoyl)-3-chlorotoluene

HRID 280638Notes

Reaction equation

HRID 280638 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[Cl-:12].[Al+3].[Cl-].[Cl-]>ClC1C=CC=CC=1>[Cl:12][C:2]1[CH:10]=[CH:9][C:8]([C:4]([C:3]2[CH:7]=[CH:8][C:9]([CH3:11])=[CH:10][C:2]=2[Cl:1])=[O:5])=[CH:7][CH:3]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 150651862-Chloro-4-methylbenzoyl chloride

Product 1

HCID 136496494-(4-Chlorobenzoyl)-3-chlorotolueneYield 152.8%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
80 °C

Procedure

A stirred 80° C. solution of 2-chloro-4-methylbenzoyl chloride (6.6 g, 39 mmol) in chlorobenzene (10 ml) was treated with aluminum chloride (5.14 g, 38.5 mmol) in portions over 15 minutes. The mixture was stirred 15 hours at 80° C., cooled, quenched by addition of ice and concentrated hydrochloric acid (5 ml), and extracted three times with diethyl ether. The combined extracts were washed with water and saturated aqueous sodium bicarbonate, dried over anhydrous magnesium sulfate, and evaporated under vacuum. The residue was chromatographed on a column of silica gel (250 g) eluted with 7:3 (v/v) n-hexane-dichloromethane to provide 7.9 g (76%) of 4-(4-chlorobenzoyl)-3-chlorotoluene, m.p. 58°-60.5° C.

Workup

  1. temperaturecooled
  2. customquenched by addition of ice and concentrated hydrochloric acid (5 ml)
  3. extractionextracted three times with diethyl ether
  4. washThe combined extracts were washed with water and saturated aqueous sodium bicarbonate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under vacuum
  7. customThe residue was chromatographed on a column of silica gel (250 g)
  8. washeluted with 7:3 (v/v) n-hexane-dichloromethane

Sources & evidence

ORD record
ord-4318ea334fc344b18de9a8df07c57100
Source dataset
uspto-grants-1986_05
Patent number
US04590201

Reaction notes

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