Reaction #2026

ord-987cbce73ecd44fa89c19bbd9f39470c

Reaction equation

BrCCBr
1,2-dibromoethane
O=S([O-])[O-].[Na+].[Na+]
sodium sulfite
→
O=S(=O)([O-])CCS(=O)(=O)[O-].[Na+].[Na+]
title compound
Yield 65.1%
O=S(=O)([O-])CCS(=O)(=O)[O-].[Na+].[Na+]
Sodium ethane-1,2-disulfonate
Yield 65.1%

Reactants

BrCCBr
1,2-dibromoethane
O=S([O-])[O-].[Na+].[Na+]
sodium sulfite

Reagents

None

Solvents

O
water

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturewas heated
  2. 2
    Temperatureat reflux temperature for 20 h
  3. 3
    TemperatureAfter the mixture was cooled in the refrigerator, crystals
  4. 4
    Otherwere collected
  5. 5
    OtherThe crude product was repeatedly recrystallized from water-ethanol
  6. 6
    OtherThe trace amount of inorganic salts was removed
  7. 7
    workup.ADDITIONby treating the aqueous solution with a small amount of silver(I) oxide and barium hydroxide
  8. 8
    workup.ADDITIONtreated three times with Amberlite-120 (sodium form) ion-exchange resin
  9. 9
    OtherAfter removal of the water
  10. 10
    Otherthe product was recrystallized from water-ethanol

Procedure

A mixture of 1,2-dibromoethane (37.6 g, 0.20 mol) and sodium sulfite (63.0 g, 0.5 mol) in water (225 mL) was heated at reflux temperature for 20 h. After the mixture was cooled in the refrigerator, crystals were collected. The crude product was repeatedly recrystallized from water-ethanol. The trace amount of inorganic salts was removed by treating the aqueous solution with a small amount of silver(I) oxide and barium hydroxide. The basic solution was neutralized with Amberlite-120 ion-exchange resin and treated three times with Amberlite-120 (sodium form) ion-exchange resin. After removal of the water, the product was recrystallized from water-ethanol to afford the title compound (30.5 g).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05728375uspto-grants-1998_03