Ethanol → Sodium 6-bromohexanesulfonate

HRID 861900Notes

Reaction equation

HRID 861900 reaction equation
[Br:1][CH:2](Br)[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C(O)C.[S:12]([O-:15])([O-:14])=[O:13].[Na+:16].[Na+]>O>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][S:12]([O-:15])(=[O:14])=[O:13].[Na+:16]

Participants

5

Reactant 3

HCID 702EthanolHCID 24437Sodium SulfiteHCID 118068541,1-Dibromohexane

Product 1

HCID 23667833Sodium 6-bromohexanesulfonate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of dibromohexane (81.0 g), ethanol (120 ml) and water (50 ml) is added dropwise an aqueous solution (50 ml) of sodium sulfite (12.5 g) under reflux over 2 hours. After additional refluxing for 2 hours, the reaction mixture is allowed to cool and unreacted dibromohexane is removed and then the resulting solution is concentrated under reduced pressure. 95% Ethanol (200 ml) is added and the mixture is allowed to cool at room temperature overnight and precipitated crystals are collected by filtration to give the title compound as colorless prisms. The filtrate is concentrated and is allowed to cool overnight and precipitated crystals are collected by filtration to give additional title compound.

Workup

  1. temperatureunder reflux over 2 hours
  2. temperatureAfter additional refluxing for 2 hours
  3. temperatureto cool
  4. customunreacted dibromohexane is removed
  5. concentrationthe resulting solution is concentrated under reduced pressure
  6. addition95% Ethanol (200 ml) is added
  7. customprecipitated crystals
  8. filtrationare collected by filtration

Sources & evidence

ORD record
ord-f3937c2cb16d4499aca090e31f501521
Source dataset
uspto-grants-1998_02
Patent number
US05716950

Reaction notes

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