Phosphorus pentachloride → Ethyl 6-(chlorosulfonyl)hexanoate

HRID 226179Notes

Reaction equation

HRID 226179 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 6-ethoxy-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-4d3eafc5548d489b884a0e8cbacc12a6
Source dataset
uspto-grants-2009_07
Patent number
US07557140B2

Reaction notes

Loading…