Potassium Iodide → HCID 14330002, compound

HRID 2164917Notes

Reaction equation

HRID 2164917 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:14])[CH3:13])=[C:8]([OH:15])[C:7]=1[CH2:16][CH2:17][CH3:18].[CH2:20]([CH:22]1[O:24][CH2:23]1)Br.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CN(C)C=O>[CH3:1][O:2][C:3](=[O:19])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:14])[CH3:13])=[C:8]([O:15][CH2:20][CH:22]2[CH2:23][O:24]2)[C:7]=1[CH2:16][CH2:17][CH3:18]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 13763323Methyl (4-acetyl-3-hydroxy-2-propylphenoxy)acetate

Product 1

HCID 14330002HCID 14330002, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 7.75 g of (4-acetyl-3-hydroxy-2-propylphenoxy)acetic acid methyl ester, 7.5 ml of epibromohydrin, 4.8 g of potassium iodide and 6.0 g of anhydrous potassium carbonate in 80 ml of anhydrous acetone and 40 ml of anhydrous dimethylformamide was stirred at reflux for 50 hours. The reaction mixture was filtered and the filtrate was concentrated in vacuo to an oil which was purified by high pressure liquid chromatography (HPLC) using 10% ethyl acetate-hexane to yield 6.16 g of [4-acetyl-3-(oxiranylmethoxy)-2-propylphenoxy]acetic acid methyl ester.

Workup

  1. temperatureat reflux for 50 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo to an oil which
  4. customwas purified by high pressure liquid chromatography (HPLC)

Sources & evidence

ORD record
ord-6a89ffda3d374e5c96af630bc0a2afda
Source dataset
uspto-grants-1985_03
Patent number
US04507498

Reaction notes

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