Water → HCID 54068547, compound

HRID 582386Notes

Reaction equation

HRID 582386 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.[C:21]1(C)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[OH2:28]>[Fe](Cl)(Cl)Cl>[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]=[C:16]([O:28][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]([O:19][CH3:20])=[CH:14][C:13]=1[CH3:12])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 75303-MethoxytolueneHCID 783922,6-Dichlorobenzoyl chloride

Product 1

HCID 54068547HCID 54068547, compound

Reagents, catalysts & solvents 1

HCID 24380Iron chloride (FeCl3)Catalyst

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-3a065557af014557885d239da425cb2d
Source dataset
uspto-grants-1999_07
Patent number
US05922919

Reaction notes

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