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

HRID 1744019Notes

Reaction equation

HRID 1744019 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-b9a37bbc8ecc455c92f5d77e1b5c1f9d
Source dataset
uspto-grants-2006_03
Patent number
US07012152B2

Reaction notes

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