Sodium Iodide → HCID 20442205, compound

HRID 1632748Notes

Reaction equation

HRID 1632748 reaction equation
[I-:1].[Na+].C1(C)C=CC(S(O[CH2:13][CH:14]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:15][O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])(=O)=O)=CC=1>CC(C)=O>[CH2:26]([O:25][CH:14]([CH2:15][O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:13][I:1])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 20442238HCID 20442238, compound

Product 1

HCID 20442205HCID 20442205, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Sodium iodide (4.07 g) was added to a stirred solution of 2,3-di-n-octyloxy-1-propyl p-toluenesulfonate (860 mg) in acetone (14 ml) at room temperature and heated under reflux for 11 hours. The resultant mixture was evaporated under reduced pressure, and the residue was dissolved in a mixture of water (20 ml) and diethyl ether (10 ml). The aqueous solution was separated and extracted with diethyl ether, and then the organic layer and the extract were combined. The organic solution was washed with a saturated aqueous solution of sodium chloride twice, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give oil (620 mg) of 2,3-di-n-octyloxy-1-propyl iodide.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 11 hours
  3. customThe resultant mixture was evaporated under reduced pressure
  4. dissolutionthe residue was dissolved in a mixture of water (20 ml) and diethyl ether (10 ml)
  5. customThe aqueous solution was separated
  6. extractionextracted with diethyl ether
  7. washThe organic solution was washed with a saturated aqueous solution of sodium chloride twice
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-bcf498048abd48a7a3d7b1fc32ed6e5a
Source dataset
uspto-grants-1984_10
Patent number
US04477447

Reaction notes

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