Sodium Iodide → Iodomethyl pivalate

HRID 1981635Notes

Reaction equation

HRID 1981635 reaction equation
[I-:1].[Na+].[O:3]1[CH2:8]CCOO1.[C:9](Cl)(=[O:14])C(C)(C)C.CCC[CH2:19][CH2:20][CH3:21].[C:22](#N)C>O>[C:9]([O:3][CH2:8][I:1])(=[O:14])[C:20]([CH3:19])([CH3:21])[CH3:22]

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 8058HexaneHCID 62493Pivaloyl chlorideHCID 19593658CID 19593658

Product 1

HCID 104401Iodomethyl pivalateYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 4.5 g of sodium iodide and 1.0 g of trioxane in 30 ml of acetonitrile, 3.6 g of pivaloyl chloride is added dropwise while stirring under ice-cooling. The mixture is stirred for 60 minutes at 60° C. Fifty ml of n-hexane and 50 ml of water are added to the reaction mixture and the aqueous layer is discarded. The organic layer is washed with water once and dried over magnesium sulfate. Evaporation of the solvent gives 4.8 g of the titled compound as an oil. Yield: 66%.

Workup

  1. additionis added dropwise
  2. temperaturecooling
  3. stirringThe mixture is stirred for 60 minutes at 60° C
  4. washThe organic layer is washed with water once
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-81ba3afa3c1940299013410c23e38fbd
Source dataset
uspto-grants-1986_06
Patent number
US04593115

Reaction notes

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