Thionyl Chloride → Methyl 3-chlorocarbonyl-2,4-dichlorobenzoate

HRID 1368823Notes

Reaction equation

HRID 1368823 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[C:15]([C:16](O)=[O:17])=[C:14]([Cl:19])[CH:13]=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9]>CN(C)C=O.C1(C)C=CC=CC=1>[Cl:3][C:16]([C:15]1[C:6]([Cl:5])=[C:7]([CH:12]=[CH:13][C:14]=1[Cl:19])[C:8]([O:10][CH3:11])=[O:9])=[O:17]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 18517411HCID 18517411, compound

Product 1

HCID 18517406Methyl 3-chlorocarbonyl-2,4-dichlorobenzoateYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Procedure

2 drops of dimethylformamide and 11.90 g (0.1 mol) of thionyl chloride were added to a solution of 5.00 g (0.02 mol) of methyl 2,4-dichloro-3-hydroxycarbonylbenzoate and 50 ml of dry toluene. The solution was heated under reflux for 4 hours. Removal of the solvent by distillation gave 5.35 g of methyl 3-chlorocarbonyl-2,4-dichlorobenzoate.

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 4 hours
  3. customRemoval of the solvent
  4. distillationby distillation

Sources & evidence

ORD record
ord-5f793e16d369460e90d5794f30d8cbc0
Source dataset
uspto-grants-2003_06
Patent number
US06576596B1

Reaction notes

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