Thionyl Chloride → HCID 13923990, compound

HRID 358189Notes

Reaction equation

HRID 358189 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[C:17]([CH3:18])=[C:16]([Cl:19])[CH:15]=[CH:14][C:7]=1[O:8][CH:9]([CH3:13])[C:10](O)=[O:11]>>[Cl:5][C:6]1[C:17]([CH3:18])=[C:16]([Cl:19])[CH:15]=[CH:14][C:7]=1[O:8][CH:9]([CH3:13])[C:10]([Cl:3])=[O:11]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 133669662-(2,4-Dichloro-3-methylphenoxy)propanoic acid

Product 1

HCID 13923990HCID 13923990, compoundYield 106.2%

Procedure

Thionyl chloride (17.9 g; 0.15 mole) was added to 12.5 g (0.05 mole) of 2-(2,4-dichloro-3-methylphenoxy)-propionic acid, and the mixture was heated under reflux for 3 hours. The excess of thionyl chloride was distilled off from the reaction mixture to give 14.2 g of crude 2-(2,4-dichloro-3-methylphenoxy)propionyl chloride. A solution of 14.2 g of the crude chloride in 50 ml of diethyl ether was added dropwise to a mixture of 4.65 g (0.05 mole) and 40 g (0.05 mole) of a 5% aqueous solution of sodium hydroxide with stirring over the course of 15 minutes. The mixture was then stirred at room temperature for 1 hour. The precipitated solid was collected by filtration, washed with water and dried. Recrystallization from hexane yielded 10.7 g of the desired product as colorless needles. Yield: 66.0%; melting point 147.5 to 148.0° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. distillationThe excess of thionyl chloride was distilled off from the reaction mixture

Sources & evidence

ORD record
ord-7b1f635064a1418ca8669ca8e0ba7588
Source dataset
uspto-grants-1984_08
Patent number
US04465507

Reaction notes

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