Potassium Iodide → HCID 13520782, compound

HRID 847371Notes

Reaction equation

HRID 847371 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[O:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:23][CH2:24][NH:25][C:26](=[O:30])[O:27][CH2:28][CH3:29].[I-].[K+]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:23][CH2:24][NH:25][C:26](=[O:30])[O:27][CH2:28][CH3:29])=[CH:8][CH:7]=1

Participants

5

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 80621Ethyl 2-chloroethylcarbamateHCID 197758734-(3-Chlorophenoxy)phenol

Product 1

HCID 13520782HCID 13520782, compound

Procedure

To a solution of 13.2 g of 4-(3-chlorophenoxy)phenol (m.p. 53°-54° C.) are added 16.6 g of finely powdered potassium carbonate, 13.6 g of ethyl 2-chloroethylcarbamate and 1 g of powdered potassium iodide. With stirring, the reaction mixture is heated to +95° C. over 15 hours and then filtered. The filtrate is taken up in ice-water and extracted three times with ether. The organic extracts are washed with water, dried over sodium sulfate and concentrated by evaporation. The crude product is purified by chromatography over silica gel with a 1:3 mixture of ether/hexane to give the pure ethyl 2-[4-(3-chlorophenoxy)phenoxy]ethylcarbamate of m.p. 45°-46° C. The 1H-NMR spectrum is in conformity with the indicated structure.

Workup

  1. temperaturethe reaction mixture is heated to +95° C. over 15 hours
  2. filtrationfiltered
  3. extractionextracted three times with ether
  4. washThe organic extracts are washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated by evaporation
  7. customThe crude product is purified by chromatography over silica gel with a 1:3 mixture of ether/hexane

Sources & evidence

ORD record
ord-a0740898f3c84e86beedeb3873d8930e
Source dataset
uspto-grants-1992_08
Patent number
US05141956

Reaction notes

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