Thionyl Chloride → 2,4,4,4-Tetrachlorobutanoyl chloride

HRID 894879Notes

Reaction equation

HRID 894879 reaction equation
[Cl:1][CH:2]([CH2:6][C:7]([Cl:10])([Cl:9])[Cl:8])[C:3](O)=[O:4].S(Cl)([Cl:13])=O>CN(C)C=O>[Cl:1][CH:2]([CH2:6][C:7]([Cl:10])([Cl:9])[Cl:8])[C:3]([Cl:13])=[O:4]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 123867212,4,4,4-Tetrachlorobutyric acid

Product 1

HCID 30178312,4,4,4-Tetrachlorobutanoyl chlorideYield 93.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

226 g (1 mol) of 2,4,4,4-tetrachlorobutyric acid [produced according to CA, 63, 13089e (1965)], 600 g of thionyl chloride and 1 ml of N,N-dimethylformamide are heated for 2 hours at 50° C. and for 2 hours at 75° C. After the unreacted thionyl chloride has been evaporated off, the residue is distilled to obtain 227.6 g (93% of theory) of 2,4,4,4-tetrachlorobutyric acid chloride; b.p. 90°-91° C./15 mm Hg.

Workup

  1. customAfter the unreacted thionyl chloride has been evaporated off
  2. distillationthe residue is distilled

Sources & evidence

ORD record
ord-3d0a19e8af1846fd8bb8dc41512de99f
Source dataset
uspto-grants-1981_08
Patent number
US04284821

Reaction notes

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