(4-Chlorophenyl)acetic acid → 4-Chlorophenylacetyl chloride

HRID 463770Notes

Reaction equation

HRID 463770 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.S(Cl)([Cl:14])=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([Cl:14])=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 15880(4-Chlorophenyl)acetic acidHCID 24386Thionyl Chloride

Product 1

HCID 906924-Chlorophenylacetyl chlorideYield 40.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred suspension of 4-chlorophenylacetic acid (85.3 g) in 500 ml of toluene, 45 ml of thionyl chloride (74.4 g) are added. The resulting mixture is stirred at RT, heated slowly to boiling, and stirred overnight under reflux. After cooling the reaction mixture to RT, the solvent is evaporated in vacuo. Distillation of the residue affords 38.15 g of a red liquid.

Workup

  1. additionare added
  2. temperatureheated slowly
  3. stirringstirred overnight
  4. temperatureunder reflux
  5. temperatureAfter cooling the reaction mixture to RT
  6. customthe solvent is evaporated in vacuo
  7. distillationDistillation of the residue

Sources & evidence

ORD record
ord-67e6c2321a5f44c19eb280e3e1a490c0
Source dataset
uspto-grants-1985_10
Patent number
US04544670

Reaction notes

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