Potassium Iodide → [4-Acetyl-3-[2-(2-chloroethoxy)ethoxy]-2-propylphenoxy]acetic acid ethyl ester

HRID 2164931Notes

Reaction equation

HRID 2164931 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[C:9]([OH:16])[C:8]=1[CH2:17][CH2:18][CH3:19])[CH3:2].[Cl:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26]Cl.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O.CN(C)C=O>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[C:9]([O:16][CH2:26][CH2:25][O:24][CH2:23][CH2:22][Cl:21])[C:8]=1[CH2:17][CH2:18][CH3:19])[CH3:2]

Participants

7

Reactant 4

HCID 4875Potassium Iodide2×HCID 8115Bis(2-chloroethyl) etherHCID 11430Potassium Carbonate3×HCID 13389144Ethyl (4-acetyl-3-hydroxy-2-propylphenoxy)acetate

Product 1

HCID 14330006[4-Acetyl-3-[2-(2-chloroethoxy)ethoxy]-2-propylphenoxy]acetic acid ethyl esterYield 72%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 6.0 g of (4-acetyl-3-hydroxy-2-propylphenoxy)acetic acid ethyl ester, 25 ml of bis(2-chloroethyl)ether and 2.2 g of anhydrous potassium carbonate in 150 ml of anhydrous acetone was stirred at reflux. After 24 hours, 2 g of potassium iodide and 50 ml of anhydrous dimethylformamide were added and reflux was continued. After 50 hours, 2.2 g of potassium carbonate and 2 g of potassium iodide were added and after 77 hours, 2.0 g of potassium carbonate was added. After a total reflux time of 108 hours, the reaction mixture was concentrated in vacuo and the residue was purified by high pressure liquid chromatography using 25% ethyl acetate-hexane to give 5.96 g (72% yield) of [4-acetyl-3-[2-(2-chloroethoxy)ethoxy]-2-propylphenoxy]acetic acid ethyl ester as an oil.

Workup

  1. temperatureat reflux
  2. temperaturereflux
  3. waitAfter 50 hours
  4. concentrationAfter a total reflux time of 108 hours, the reaction mixture was concentrated in vacuo
  5. customthe residue was purified by high pressure liquid chromatography

Sources & evidence

ORD record
ord-2d13c7216a6b4b9686a238de66c3d21e
Source dataset
uspto-grants-1985_03
Patent number
US04507498

Reaction notes

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