Phosphorus pentachloride → Ethyl 6-(chlorosulfonyl)hexanoate

HRID 2217702Notes

Reaction equation

HRID 2217702 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-f3fbb10239a342fba200ea8e91f425a4
Source dataset
uspto-grants-2008_08
Patent number
US07407988B2

Reaction notes

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