Phosphorus pentachloride → Ethyl 6-(chlorosulfonyl)hexanoate

HRID 351085Notes

Reaction equation

HRID 351085 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][S:10]([O-])(=[O:12])=[O:11])[CH3:2].[Na+].P(Cl)(Cl)(Cl)(Cl)[Cl:17]>>[Cl:17][S:10]([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:14])(=[O:12])=[O:11]

Participants

3

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 23703551HCID 23703551, compound

Product 1

HCID 22492402Ethyl 6-(chlorosulfonyl)hexanoateYield 61%

Procedure

Sodium 6ethoxy-6-oxo-1-hexanesulfonate (62b) (1.68 g, 6.8 mmol) was mixed with phosphorus pentachloride and the mixture was carefully pestled in a mortar. After the reaction came to the end (the foaming of the reaction mixture ceased) the mixture was extracted with dry benzene (50 ml). The extract was evaporated under reduced pressure and the residue was dried in vacuum to give crude title compound (1.03 g, 61%) as a hygroscopic oil. The chloride (63b) was used in further reactions without additional purification.

Workup

  1. extractionwas extracted with dry benzene (50 ml)
  2. customThe extract was evaporated under reduced pressure
  3. customthe residue was dried in vacuum

Sources & evidence

ORD record
ord-e7969da70bc24bcfad520d1d51bda33b
Source dataset
uspto-grants-2007_02
Patent number
US07183298B2

Reaction notes

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