Thionyl Chloride → HCID 14802144, compound

HRID 484186Notes

Reaction equation

HRID 484186 reaction equation
S(Cl)([Cl:3])=O.[C:5]([O:12][CH2:13][CH2:14][CH2:15][CH3:16])(=[O:11])[CH2:6][CH2:7][C:8]([O-])=[O:9]>CN(C=O)C>[Cl:3][C:8](=[O:9])[CH2:7][CH2:6][C:5]([O:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:11]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21868199HCID 21868199, compound

Product 1

HCID 14802144HCID 14802144, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

Excess thionyl chloride and a few drops of DMF are added to monobutyl succinate. The reaction starts with evolution of gas. The mixture is stirred overnight with the exclusion of moisture and the excess thionyl chloride is then removed by distillation at normal pressure. The crude product which remains is fractionally distilled at 0.05 mbar and the pure product is obtained at about 70° C. In the IR-spectroscopic characterization, the product has bands at 1,800 cm-1 (acid chloride) and 1,740 cm-1 (ester) of equal intensity.

Workup

  1. customthe excess thionyl chloride is then removed by distillation at normal pressure
  2. distillationThe crude product which remains is fractionally distilled at 0.05 mbar
  3. customthe pure product is obtained at about 70° C

Sources & evidence

ORD record
ord-441309bcd3184bcaa1faf7614629ccd2
Source dataset
uspto-grants-1993_07
Patent number
US05229469

Reaction notes

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