Thionyl Chloride → 2-(2,6-Dichlorophenyl)acetyl chloride

HRID 463778Notes

Reaction equation

HRID 463778 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:7]=1[CH2:13][C:14]([OH:16])=O>C1(C)C=CC=CC=1>[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:7]=1[CH2:13][C:14]([Cl:3])=[O:16]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 810582,6-Dichlorophenylacetic acid

Product 1

HCID 27581482-(2,6-Dichlorophenyl)acetyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

30.93 g of thionyl chloride are added dropwise to a warmed, mechanically stirred mixture of 45.12 g of 2,6-dichlorophenylacetic acid in 125 ml of toluene. The reaction mixture is then maintained at reflux for 5 hrs and cooled overnight at RT. The reaction mixture is concentrated in vacuo and the concentrate dissolved in hot petroleum ether and the solids filtered. The filtrate is concentrated in vacuo to give a dark amber liquid, which is distilled to give a clear pinkish liquid.

Workup

  1. temperatureThe reaction mixture is then maintained
  2. temperatureat reflux for 5 hrs
  3. concentrationThe reaction mixture is concentrated in vacuo
  4. dissolutionthe concentrate dissolved in hot petroleum ether
  5. filtrationthe solids filtered
  6. concentrationThe filtrate is concentrated in vacuo
  7. customto give a dark amber liquid, which
  8. distillationis distilled
  9. customto give a clear pinkish liquid

Sources & evidence

ORD record
ord-9c6f3cc32d0b4d0190c16567badbd980
Source dataset
uspto-grants-1985_10
Patent number
US04544670

Reaction notes

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