Thionyl Chloride → o-Iodophenylacetyl chloride

HRID 894395Notes

Reaction equation

HRID 894395 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=O.S(Cl)([Cl:14])=O>C1C=CC=CC=1>[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([Cl:14])=[O:11]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 27800902-Iodophenylacetic acid

Product 1

HCID 10934858o-Iodophenylacetyl chlorideYield 90.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To 10 g (0.038 mole) of o-iodophenylacetic acid was added 50 ml of a solution of 5.7 g (0.048 mole) of thionyl chloride in anhydrous benzene, and the mixture was refluxed for 2 hours under agitation. Then, the solvent and unreacted thionyl chloride were removed by distillation under reduced pressure below 40° C. and the residue was subjected to distillation under reduced pressure to obtain 9.6 g of o-iodophenylacetyl chloride as a light yellow oily product having a boiling point of 153° to 156° C. under 8 mmHg in a yield of 90%.

Workup

  1. temperaturethe mixture was refluxed for 2 hours under agitation
  2. customThen, the solvent and unreacted thionyl chloride were removed by distillation under reduced pressure below 40° C.
  3. distillationthe residue was subjected to distillation under reduced pressure

Sources & evidence

ORD record
ord-1848dda1317b47a89389afa5ff2b3b86
Source dataset
uspto-grants-1981_08
Patent number
US04283532

Reaction notes

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