Water → 1-Iodo-4-methyl-4-nitro-pentane

HRID 432991Notes

Reaction equation

HRID 432991 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][C:9]([CH3:14])([N+:11]([O-:13])=[O:12])[CH3:10])(=O)=O.[I-:15].[Na+].O>CC(C)=O>[CH3:10][C:9]([N+:11]([O-:13])=[O:12])([CH3:14])[CH2:8][CH2:7][CH2:6][I:15]

Participants

5

Reactant 3

HCID 962WaterHCID 5238Sodium IodideHCID 130471214-Methyl-4-nitropentyl methanesulfonate

Product 1

HCID 99430631-Iodo-4-methyl-4-nitro-pentaneYield 99.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Methyl-4-nitropentanol methanesulfonate (3.38 g, 15 mmol) was dissolved in acetone (50 ml) and sodium iodide (8.7 g, 58 mmol) was added. The mixture was stirred overnight. Water (20 ml) was added and acetone was evaporated by concentration under reduced pressure. The residue was extracted with ethyl acetate (50 ml). The extract was washed with 5% aqueous sodium thiosulfate solution (20 ml) and saturated brine (20 ml), and ethyl acetate was evaporated by concentration under reduced pressure to give the objective compound (3.84 g, yield 99.6%).

Workup

  1. customacetone was evaporated by concentration under reduced pressure
  2. extractionThe residue was extracted with ethyl acetate (50 ml)
  3. washThe extract was washed with 5% aqueous sodium thiosulfate solution (20 ml) and saturated brine (20 ml), and ethyl acetate
  4. customwas evaporated by concentration under reduced pressure

Sources & evidence

ORD record
ord-084abec90d204b638ecc24bdcab17c62
Source dataset
uspto-grants-2003_12
Patent number
US06664412B2

Reaction notes

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