Thionyl Chloride → p-Chlorophenoxyacetyl chloride

HRID 1283613Notes

Reaction equation

HRID 1283613 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:16]=[CH:15][C:9]([O:10][CH2:11][C:12](O)=[O:13])=[CH:8][CH:7]=1>C1C=CC=CC=1>[Cl:5][C:6]1[CH:16]=[CH:15][C:9]([O:10][CH2:11][C:12]([Cl:3])=[O:13])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl Chloride2×HCID 26229(4-Chlorophenoxy)acetic acid

Product 1

HCID 77771p-Chlorophenoxyacetyl chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Thionyl chloride (0.431 mole, 51.26 grams) was slowly added to p-chlorophenoxyacetic acid (0.287 mole, 53.5 grams) in 160 ml of benzene at room temperature. The reaction mixture was refluxed for 18 hours. The excess thionyl chloride and benzene were stripped from reaction mixture under vacuum (aspirator) and the residue p-chlorophenoxyacetyl chloride was distilled at 70°C./0.05 mm Hg.

Workup

  1. temperatureThe reaction mixture was refluxed for 18 hours
  2. distillationthe residue p-chlorophenoxyacetyl chloride was distilled at 70°C./0.05 mm Hg

Sources & evidence

ORD record
ord-953b7956a7004363bedd30e27d78d384
Source dataset
uspto-grants-1976_08
Patent number
US03975532

Reaction notes

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