2-Chloroethyl vinyl ether → HCID 21487831, compound

HRID 1414524Notes

Reaction equation

HRID 1414524 reaction equation
[CH:1]1[C:14]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[Na].[H-].[Na+].[CH:18]([O:20][CH2:21][CH2:22]Cl)=[CH2:19]>CS(C)=O.O>[CH:18]([O:20][CH2:21][CH2:22][C:13]1([CH2:22][CH2:21][O:20][CH:18]=[CH2:19])[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[S:6][C:5]2[C:14]1=[CH:1][CH:2]=[CH:3][CH:4]=2)=[CH2:19]

Participants

7

Reactant 4

HCID 80742-Chloroethyl vinyl etherHCID 24758Sodium hydrideHCID 67495ThioxantheneHCID 5360545Sodium

Product 1

HCID 21487831HCID 21487831, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A solution of thioxanthene (29.7 g.) in dimethyl sulphoxide (1,200 ml.) is added gradually to a solution of sodium methylsulphinylmethide [prepared in the usual way from sodium hydride (24 g. of a 60% dispersion in mineral oil) and dimethyl sulphoxide (300 ml.)]. The dark red mixture is cooled in ice and chloroethyl vinyl ether (44 g.) is added dropwise. The mixture is stirred under nitrogen for a further 16 hours, allowed to warm to ambient temperature (18°to 20° C.), poured into water (3 1.) and extracted with ether. The ethereal solution is washed with water, dried, and then evaporated to give crude oily 9,9-bis(2'-vinyloxyethyl)thioxanthene.

Workup

  1. temperatureThe dark red mixture is cooled in ice
  2. extractionextracted with ether
  3. washThe ethereal solution is washed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-5eab31ea741d46ba94329bdd900cf253
Source dataset
uspto-grants-1977_01
Patent number
US04001418

Reaction notes

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