Sodium Iodide → 4'-(2-Iodoethyl)octanophenone

HRID 1595063Notes

Reaction equation

HRID 1595063 reaction equation
C1(C)C=CC(S(O[CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19](=[O:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:15][CH:14]=2)(=O)=O)=CC=1.[I-:29].[Na+]>CC(=O)CC>[I:29][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 110477072-(4-Octanoyl phenyl)ethyl p-toluene sulfonate

Product 1

HCID 111320764'-(2-Iodoethyl)octanophenoneYield 99.6%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

2-(4-Octanoyl phenyl)ethyl p-toluene sulfonate (1.23 g) prepared in the above-described procedure was dissolved in 2-butanone (18 ml) to obtain a solution. Sodium iodide (550 mg) was added to the solution, and the solution was heated to reflux for 40 minutes. The reaction solution was concentrated, and the solution was partitioned with water-dichloromethane. The dichloromethane layer was washed with water, dried over anhydrous sodium sulfate, and concentrated to obtain 4′-(2-iodoethyl)octanophenone (1.09 g) in the form of white crystal.

Workup

  1. customto obtain a solution
  2. temperaturethe solution was heated
  3. temperatureto reflux for 40 minutes
  4. concentrationThe reaction solution was concentrated
  5. customthe solution was partitioned with water-dichloromethane
  6. washThe dichloromethane layer was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-fd59c733aa02429cb128b339a920c260
Source dataset
uspto-grants-2001_09
Patent number
US06284915B1

Reaction notes

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