Thionyl Chloride → HCID 14802144, compound

HRID 1612894Notes

Reaction equation

HRID 1612894 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 one drop of DMF are added to monobutyl succinate. The reaction takes place with evolution of gas. The mixture is left to stir with exclusion of moisture overnight and subsequently the excess thionyl chloride is removed by distillation under atmospheric pressure. The remaining crude product is fractionally distilled under 0.05 mbar, and the pure product is obtained at about 70° C. The characterization of the product by IR spectroscopy shows bands at 1800 cm-1 (acid chloride) and 1740 cm-1 (ester) of equal intensity.

Workup

  1. waitThe mixture is left
  2. customsubsequently the excess thionyl chloride is removed by distillation under atmospheric pressure
  3. distillationThe remaining crude product is fractionally distilled under 0.05 mbar
  4. customthe pure product is obtained at about 70° C

Sources & evidence

ORD record
ord-cbf56ac71687479fbcfed6ba1b36d52f
Source dataset
uspto-grants-1993_03
Patent number
US05190982

Reaction notes

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