Sodium Iodide → Iodomethyl pivalate

HRID 727508Notes

Reaction equation

HRID 727508 reaction equation
[I-:1].[Na+].[CH3:3][C:4]([CH3:11])([CH3:10])[C:5]([O:7][CH2:8]Cl)=[O:6]>C(#N)C>[CH3:3][C:4]([CH3:11])([CH3:10])[C:5]([O:7][CH2:8][I:1])=[O:6]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 87885Chloromethyl pivalate

Product 1

HCID 104401Iodomethyl pivalateYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Sodium iodide (dried) (15.0 g, 100 mmol) was added in one portion to a solution of 2,2-dimethylpropanoic acid, chloromethyl ester (10.0 g, 66.7 mmol) in dry acetonitrile (80 mL) at RT under argon. The heterogeneous reaction was stirred at RT for 6 h, then concentrated in vacuo. The residue was partitioned between toluene (150 mL) and 5% sodium bisulfite (40 mL). The organic layer was washed with 5% sodium bisulfite (40 mL) and water (20 mL), then dried over MgSO4. Evaporation gave title iodide (12.1 g, 75%) as a pale yellow oil.

Workup

  1. customThe heterogeneous reaction
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between toluene (150 mL) and 5% sodium bisulfite (40 mL)
  4. washThe organic layer was washed with 5% sodium bisulfite (40 mL) and water (20 mL)
  5. dry with materialdried over MgSO4
  6. customEvaporation

Sources & evidence

ORD record
ord-f2c474b017634c3a8dbee159b0c6cc73
Source dataset
uspto-grants-1998_01
Patent number
US05712396

Reaction notes

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