Thionyl Chloride → 1-Pentanesulfonyl chloride

HRID 902237Notes

Reaction equation

HRID 902237 reaction equation
[CH2:1]([S:6]([OH:9])(=O)=[O:7])[CH2:2][CH2:3][CH2:4][CH3:5].[Na].S(Cl)([Cl:13])=O>>[CH2:1]([S:6]([Cl:13])(=[O:9])=[O:7])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 898271-Pentanesulfonic acidHCID 5360545Sodium

Product 1

HCID 2375551-Pentanesulfonyl chlorideYield 61%

Conditions

Temperature
60 °C

Procedure

1-Pentanesulfonic acid, sodium salt (10 g, 57.5 mmol) was charged into a 250 ml round bottom flask (allow headroom). Thionyl chloride (20 mL) is added; gas evolves, and a while solid forms. The mixture is heated at 60° C. for 3 hours. The solvents are removed in vacuo; toluene is added and removed in vacuo to remove residue of SOCl2. The residue is partitioned between CH2Cl2 and ice water; the organic layer is dried over Na2SO4. The crude product is purified by distillation (bp 54-56° C. @ 0.5 mm Hg) to give a clear oil, 61% yield.

Workup

  1. customThe solvents are removed in vacuo
  2. additiontoluene is added
  3. customremoved in vacuo
  4. customto remove residue of SOCl2
  5. customThe residue is partitioned between CH2Cl2 and ice water
  6. dry with materialthe organic layer is dried over Na2SO4
  7. distillationThe crude product is purified by distillation (bp 54-56° C. @ 0.5 mm Hg)
  8. customto give a clear oil, 61% yield

Sources & evidence

ORD record
ord-5125f71b0c1e42e2885c56215e531849
Source dataset
uspto-grants-2008_04
Patent number
US07365093B2

Reaction notes

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