Ethanol → 5-Bromo-1-pentanesulfonic Acid Sodium Salt

HRID 1611675Notes

Reaction equation

HRID 1611675 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]Br.C(O)C.[S:11]([O-:14])([O-:13])=[O:12].[Na+:15].[Na+]>O>[Na+:15].[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][S:11]([O-:14])(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 702EthanolHCID 81001,5-DibromopentaneHCID 24437Sodium Sulfite

Product 1

HCID 236678325-Bromo-1-pentanesulfonic Acid Sodium SaltYield 45%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 1,5-dibromopentane (23.2 g, 101 mmol), ethanol (40 mL) and water (40 mL) was dropwise added a solution of sodium sulfite (4.24 g, 33.6 mmol) in water (15 mL) under heating under reflux over 2 hr. After heating under reflux for 2 hr, the solvent was distilled away under reduced pressure and n-hexane/ethanol was added. The precipitated crystals were washed with n-hexane and dried in vacuo to give the title compound (3.81 g, 45%).

Workup

  1. temperatureunder heating
  2. temperatureunder reflux over 2 hr
  3. temperatureAfter heating
  4. temperatureunder reflux for 2 hr
  5. distillationthe solvent was distilled away under reduced pressure and n-hexane/ethanol
  6. additionwas added
  7. washThe precipitated crystals were washed with n-hexane
  8. customdried in vacuo

Sources & evidence

ORD record
ord-6b17709b3fce44e6b5e0eb717ca3f581
Source dataset
uspto-grants-2006_01
Patent number
US06989401B2

Reaction notes

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