Toluene → 2,6-Dichloro-4'-methoxy-2'-methyl-benzophenone

HRID 965462Notes

Reaction equation

HRID 965462 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].[CH3:12][C:13]1[CH:14]=[C:15]([O:19][CH3:20])[CH:16]=[CH:17][CH:18]=1.C1(C)C=CC=CC=1>[Fe](Cl)(Cl)Cl.O>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4]([C:18]1[CH:17]=[CH:16][C:15]([O:19][CH3:20])=[CH:14][C:13]=1[CH3:12])=[O:5]

Participants

6

Reactant 3

HCID 1140TolueneHCID 75303-MethoxytolueneHCID 783922,6-Dichlorobenzoyl chloride

Product 1

HCID 545052582,6-Dichloro-4'-methoxy-2'-methyl-benzophenone

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2,6-dichlorobenzoylchloride (5.24 g; 25 mmol), 3-methylanisole (2.44 g; 20 mmol) and iron(III)chloride (20 mg) is heated to 100° C. for 45 minutes with stirring. After cooling, toluene is added, the mixture is shaken with water, the organic phase is dried and the solvent is evaporated. The reaction product is purified chromatograpically (flash column with 70 g of silicagel; elution with petrolether/toluene changing from 75:25 to 40:60 (v/v)). After evaporation the residue from the main fraction is treated with petrolether to give white crystalls (1.33 g; 22.5% y); mp. 89° C.

Workup

  1. temperatureAfter cooling
  2. customthe organic phase is dried
  3. customthe solvent is evaporated
  4. customThe reaction product is purified chromatograpically
  5. wash(flash column with 70 g of silicagel; elution with petrolether/toluene changing from 75:25 to 40:60 (v/v))
  6. customAfter evaporation the residue from the main fraction
  7. additionis treated with petrolether
  8. customto give white crystalls (1.33 g; 22.5% y)

Sources & evidence

ORD record
ord-8c732aa0e59449639e94b72171f7f0af
Source dataset
uspto-grants-1998_06
Patent number
US05773663

Reaction notes

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