2-Chloroethanol → HCID 86740252, compound

HRID 485215Notes

Reaction equation

HRID 485215 reaction equation
N#N.[Cl:3][CH2:4][CH2:5]O.Cl[S:8]([OH:11])(=[O:10])=[O:9].[OH-:12].[Na+:13]>CO.C(Cl)(Cl)Cl>[S:8]([O-:11])([O-:12])(=[O:10])=[O:9].[Cl:3][CH2:4][CH3:5].[Na+:13].[Na+:13]

Participants

7

Reactant 4

HCID 342-ChloroethanolHCID 947NitrogenHCID 14798Sodium HydroxideHCID 24638Chlorosulfonic acid

Product 1

HCID 86740252HCID 86740252, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
-30 °C

Procedure

A 2 liter round bottom flask was equipped with an overhead stirrer, thermometer, condenser and addition funnel with N2 lnlet. 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. temperatureto warm to room temperature
  3. temperatureThe reaction was heated
  4. temperatureto reflux
  5. filtrationfiltered hot
  6. customThe filtrate crystallized
  7. customupon standing yielding white crystals, which
  8. filtrationwere filtered
  9. washwashed with cold methanol

Sources & evidence

ORD record
ord-bf61e0851f1b4fd4bb12a834436e084c
Source dataset
uspto-grants-1985_08
Patent number
US04536309

Reaction notes

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