Sodium Iodide → HCID 129844758, compound

HRID 1379597Notes

Reaction equation

HRID 1379597 reaction equation
[I-:1].[Na+].[C:3]([O:6][C:7]1([CH2:16]Cl)[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH2:8]1)(=[O:5])[OH:4]>CC(C)=O>[C:3]([O:6][C:7]1([CH2:16][I:1])[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH2:8]1)(=[O:5])[OH:4]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 129844755HCID 129844755, compound

Product 1

HCID 129844758HCID 129844758, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

5 g of sodium iodide (Aldrich) is added to a solution of 1-chloromethyl carbonate (3) in 50 ml of acetone (Aldrich), and the reaction mixture is stirred at 50° C. for 24 h. After stirring overnight, the solvent is evaporated and the residue is redissolved in diethyl ether (Fisher). The ether layer is washed successively with 10% aqueous sodium sulfite and then water, and dried over anhydrous Na2SO4. The ether layer is separated and evaporated to give 1-iodomethyl p-nitrophenol carbonate (4) as a yellow oil which is confirmed by NMR. 1H-NMR (CDCl3): 6.03 (2H, s), 7.39 (2H, d, J=9 Hz), 8.24 (2H, d, J=9 Hz).

Workup

  1. stirringAfter stirring overnight
  2. customthe solvent is evaporated
  3. dissolutionthe residue is redissolved in diethyl ether (Fisher)
  4. washThe ether layer is washed successively with 10% aqueous sodium sulfite
  5. dry with materialwater, and dried over anhydrous Na2SO4
  6. customThe ether layer is separated
  7. customevaporated

Sources & evidence

ORD record
ord-3ec7b168ce704407be1b121834a5248f
Source dataset
uspto-grants-1997_09
Patent number
US05672584

Reaction notes

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