2-Chloroethanol → HCID 86740252, compound

HRID 1380220Notes

Reaction equation

HRID 1380220 reaction equation
[Cl:1][CH2:2][CH2:3]O.C(Cl)(Cl)Cl.Cl[S:10]([OH:13])(=[O:12])=[O:11].[OH-:14].[Na+:15]>CO>[S:10]([O-:13])([O-:14])(=[O:12])=[O:11].[Cl:1][CH2:2][CH3:3].[Na+:15].[Na+:15]

Participants

6

Reactant 4

HCID 342-ChloroethanolHCID 6212ChloroformHCID 14798Sodium HydroxideHCID 24638Chlorosulfonic acid

Product 1

HCID 86740252HCID 86740252, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-30 °C

Procedure

A 2 liter round bottom flask was equipped with an overhead stirrer, thermometer, condenser and addition funnel with N2Inlet. 216 g of 2-chloroethanol and 550 cc of dry chloroform were charged to the flask and chilled to -30° C. Chlorosulfonic acid was added dropwise in one hour, and the reaction was allowed to warm to room temperature and stir for 11/2 hours. With the reaction solution again at -30° C., cold methanol was added dropwise followed by 300 g of 50% NaOH solution. The reaction was heated to reflux and filtered hot. The filtrate crystallized upon standing yielding white crystals, which were filtered and washed with cold methanol to yield sodium 2-chloroethane sulfate.

Workup

  1. customA 2 liter round bottom flask was equipped with an overhead stirrer
  2. additionthermometer, condenser and addition funnel with N2Inlet
  3. temperatureto warm to room temperature
  4. temperatureThe reaction was heated
  5. temperatureto reflux
  6. filtrationfiltered hot
  7. customThe filtrate crystallized
  8. customupon standing yielding white crystals, which
  9. filtrationwere filtered
  10. washwashed with cold methanol

Sources & evidence

ORD record
ord-8104cdd586124d8899ed4e059ae86361
Source dataset
uspto-grants-1986_04
Patent number
US04581150

Reaction notes

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