Sodium Iodide → Iodomethyl octyl carbonate

HRID 974767Notes

Reaction equation

HRID 974767 reaction equation
[C:1](=[O:14])([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[O:2][CH2:3]Cl.[I-:15].[Na+]>CC(C)=O>[C:1](=[O:14])([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[O:2][CH2:3][I:15]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 19969190Chloromethyl octyl carbonate

Product 1

HCID 19969200Iodomethyl octyl carbonateYield 72.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of chloromethyl octyl carbonate (1.14 g, 0.005 mol) in acetone (10 ml) was added sodium iodide (2.3 g, 0.015 mol). The mixture was stirred for 3 hours, concentrated invacuo, and dissolved in dichloromethane (50 ml). This solution was washed with saturated aqueous sodium chloride, aqueous sodium thiosulfate, and saturated aqueous sodium chloride, dried (sodium sulfate) and concentrated invacuo to yield iodomethyl octyl carbonate (1.14 g).

Workup

  1. concentrationconcentrated invacuo
  2. dissolutiondissolved in dichloromethane (50 ml)
  3. washThis solution was washed with saturated aqueous sodium chloride, aqueous sodium thiosulfate, and saturated aqueous sodium chloride
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated invacuo

Sources & evidence

ORD record
ord-e50a6d5bfbaf43b69f4c60a775680c32
Source dataset
uspto-grants-1997_03
Patent number
US05607691

Reaction notes

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