Sodium Iodide → Iodomethyl pivalate

HRID 1033768Notes

Reaction equation

HRID 1033768 reaction equation
[C:1]([O:7][CH2:8]Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[Na+].[I-:11]>CC(C)=O>[C:1]([O:7][CH2:8][I:11])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 87885Chloromethyl pivalate

Product 1

HCID 104401Iodomethyl pivalateYield 75%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred solution of 8.00 g (53.30 mmol) of chloromethyl pivalate in 100 mL of acetone at RT under argon was added 24.00 g (160.00 mmol) of NaI. The mixture was heated to 40° C. for 4 h at which time the solids were removed by filtration and the filtrate was evaporated. The residue was diluted with ether, washed sequentially with water, 5% Na2S2O7, brine, and dried over MgSO4. Evaporation of the solvent provided 9.60 g (75%) of title compound as a light green oil.

Workup

  1. customwere removed by filtration
  2. customthe filtrate was evaporated
  3. additionThe residue was diluted with ether
  4. washwashed sequentially with water, 5% Na2S2O7, brine
  5. dry with materialdried over MgSO4
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-7076da45bd5f40c1a4c2b6df0d43d884
Source dataset
uspto-grants-1994_05
Patent number
US05312814

Reaction notes

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