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

HRID 2049124Notes

Reaction equation

HRID 2049124 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>>[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

3

Reactant 2

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

Product 1

HCID 906924-Chlorophenylacetyl chloride

Procedure

A 50 ml flask is charged with 17.06 g p-chlorophenylacetic acid and 11.90 g thionyl chloride. A single boiling chip is added and the flask fitted with air condenser and drying tube. The reaction mixture is heated in a 45° oil bath for 24 hr then cooled to ambient temperature. Five ml of benzene is added to the solution and light materials are pumped off at room temperature and 0.5 mm Hg. The product is then distilled through a short-path vacuum distillation apparatus at 0.10 mm Hg to give p-chlorophenylacetyl chloride as a water-white product; boiling point, 63°-64°. ##STR31##

Workup

  1. additionis added
  2. customthe flask fitted with air condenser
  3. customdrying tube
  4. temperatureThe reaction mixture is heated in a 45° oil bath for 24 hr
  5. additionFive ml of benzene is added to the solution and light materials
  6. customare pumped off at room temperature
  7. distillationThe product is then distilled through a short-path vacuum distillation apparatus at 0.10 mm Hg

Sources & evidence

ORD record
ord-59e9c9778d7e463da68826c1459b162f
Source dataset
uspto-grants-1980_04
Patent number
US04196294

Reaction notes

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