Phosphorus oxychloride → Pent-4-ene-1-sulfonyl chloride

HRID 2229454Notes

Reaction equation

HRID 2229454 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH2:6]([S:11]([O-:14])(=O)=[O:12])[CH2:7][CH2:8][CH:9]=[CH2:10].[Na+]>>[CH2:6]([S:11]([Cl:3])(=[O:14])=[O:12])[CH2:7][CH2:8][CH:9]=[CH2:10]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 23670546HCID 23670546, compound

Product 1

HCID 14872245Pent-4-ene-1-sulfonyl chlorideYield 54.5%

Procedure

Phosphorus oxychloride (570.02 g) was added to sodium 4-pentene-1-sulfonate (199.18 g) at room temperature. After reflux for 3 hours, the solution was cooled in an ice bath. The reaction solution was added gradually to a large amount of ice water. After extraction with diethyl ether, the organic layer was washed with brine, dried with magnesium sulfate, and concentrated under reduced pressure to obtain 4-pentene-1-sulfonyl chloride (106.31 g) as dark brown oil.

Workup

  1. temperatureAfter reflux for 3 hours
  2. temperaturethe solution was cooled in an ice bath
  3. extractionAfter extraction with diethyl ether
  4. washthe organic layer was washed with brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c7606f03cf3c4c3fa8b27f81db33142a
Source dataset
uspto-grants-2002_07
Patent number
US06420409B1

Reaction notes

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