Ethanol → 1-Propanesulfonic acid, 3-chloro-, sodium salt

HRID 1462228Notes

Reaction equation

HRID 1462228 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4]Br.C(O)C.[S:9]([O-:12])([O-:11])=[O:10].[Na+:13].[Na+]>O>[Cl:1][CH2:2][CH2:3][CH2:4][S:9]([O-:12])(=[O:11])=[O:10].[Na+:13]

Participants

5

Reactant 3

HCID 702EthanolHCID 80061-Bromo-3-chloropropaneHCID 24437Sodium Sulfite

Product 1

HCID 236618901-Propanesulfonic acid, 3-chloro-, sodium salt

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

1-Chloro-3-bromopropane (104.0 g), ethanol (250 ml), and water (90 ml) were stirred under reflux, and a solution of sodium sulphite (25.0 g) in distilled water (90 ml) was added to the stirred refluxing reaction mixture over a period of two hours. After the addition, refluxing was continued for a further 2 hours after which the excess alcohol and 1-chloro-3-bromopropane were removed by distillation. The remaining aqueous solution was evaporated to dryness on a steam bath and the product was recrystallised from alcohol to yield sodium 3-chloro-propane-sulphonate as a white crystalline solid.

Workup

  1. temperatureunder reflux
  2. temperaturerefluxing
  3. customreaction mixture over a period of two hours
  4. additionAfter the addition
  5. temperaturerefluxing
  6. customafter which the excess alcohol and 1-chloro-3-bromopropane were removed by distillation
  7. customThe remaining aqueous solution was evaporated to dryness on a steam bath
  8. customthe product was recrystallised from alcohol

Sources & evidence

ORD record
ord-abd5ef584348488d9d3eef34b52b422a
Source dataset
uspto-grants-1984_07
Patent number
US04459416

Reaction notes

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