Aluminum(III) Chloride → HCID 13649650, compound

HRID 280642Notes

Reaction equation

HRID 280642 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[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]=[C:8]([CH3:11])[CH:9]=[CH:10][C:2]=2[Cl:1])=[O:5])=[CH:7][CH:3]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 150651872-Chloro-5-methylbenzoyl chloride

Product 1

HCID 13649650HCID 13649650, compoundYield 157.5%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
80 °C

Procedure

A stirred solution of 2-chloro-5-methylbenzoyl chloride (9.41 g, 49.8 mmol) in chlorobenzene (14 ml) at 80° C. was treated with aluminum chloride (7.32 g, 54.9 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 (5.0 ml) and extracted with diethyl ether (2×50 ml). The combined extracts were washed with water, dried over anhydrous magnesium sulfate, and evaporated under vacuum. The residue was crystallized from n-hexane to provide 10.4 g (79%) of 3-(4-chlorobenzoyl)-4-chlorotoluene, m.p. 85°-90° C. Recrystallization raised the melting point to 90°-92° C.

Workup

  1. temperaturecooled
  2. customquenched by addition of ice and concentrated hydrochloric acid (5.0 ml)
  3. extractionextracted with diethyl ether (2×50 ml)
  4. washThe combined extracts were washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under vacuum
  7. customThe residue was crystallized from n-hexane

Sources & evidence

ORD record
ord-ab14c53f88354679b5cdf49ecf6727f6
Source dataset
uspto-grants-1986_05
Patent number
US04590201

Reaction notes

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