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

HRID 2073356Notes

Reaction equation

HRID 2073356 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>C1C=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 97.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 200 g of 4-chlorophenyl acetic acid, 178.5 g of thionyl chloride and 600 ml of benzene was heated at reflux for 6 hours and then concentrated in vacuo. The residue was vacuum distilled, giving 215.8 g of 4-chlorophenyl acetyl chloride, bp 94°-95° C. (2.5 mmHg).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 hours
  3. concentrationconcentrated in vacuo
  4. distillationdistilled

Sources & evidence

ORD record
ord-efb119d5682946cf8678837844396b0e
Source dataset
uspto-grants-1990_04
Patent number
US04916237

Reaction notes

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