Acetone → (R)-3-iodo-1-phenyl-1-(2-methyl-4-acetoxyphenoxy)propane

HRID 131755Notes

Reaction equation

HRID 131755 reaction equation
Cl[CH2:2][CH2:3][C@H:4]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13](=[O:15])[CH3:14])=[CH:8][C:7]=1[CH3:16].CC(C)=O.[I-:27].[K+]>C(OCC)C>[I:27][CH2:2][CH2:3][C@H:4]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13](=[O:15])[CH3:14])=[CH:8][C:7]=1[CH3:16]

Participants

5

Reactant 3

HCID 180AcetoneHCID 4875Potassium IodideHCID 69118291(R)-3-chloro-1-phenyl-1-(2-methyl-4-acetoxyphenoxy)propane

Product 1

HCID 69118068(R)-3-iodo-1-phenyl-1-(2-methyl-4-acetoxyphenoxy)propaneYield 70%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of (R)-3-chloro-1-phenyl-1-(2-methyl-4-acetoxyphenoxy)propane (0.200 gm, 0.63 mMol) and 15 mL acetone saturated with potassium iodide was stirred at reflux under argon overnight. The reaction mixture was poured into 50 mL diethyl ether and the resulting suspension was filtered. The filtrated was washed with saturated aqueous sodium hydrogen sulfite followed by water. The remaining organic phase was dried over magnesium sulfate and concentrated under reduced pressure to provide 0.18 gm (70%) of the desired compound as a colorless oil.

Workup

  1. temperatureat reflux under argon overnight
  2. filtrationthe resulting suspension was filtered
  3. washThe filtrated was washed with saturated aqueous sodium hydrogen sulfite
  4. dry with materialThe remaining organic phase was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f3535f69c6404c8e9c6ae653fae55f7e
Source dataset
uspto-grants-2008_06
Patent number
US07384983B2

Reaction notes

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