Toluene → HCID 54505258, compound

HRID 361970

Reaction equation

HRID 361970 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 54505258HCID 54505258, compound

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 crystals (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 crystals (1.33 g; 22.5%y)

Sources & evidence

ORD record
ord-03ef2cdb6e0045279aa073cd8d8b37ea
Source dataset
uspto-grants-1999_02
Patent number
US05866722

Linked notes

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