Sodium Iodide → 7-(Iodomethyl)pentadecane

HRID 1621349Notes

Reaction equation

HRID 1621349 reaction equation
[CH2:1]([CH:7]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:8]Cl)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[I-:18].[Na+]>CC(C)=O>[CH2:1]([CH:7]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:8][I:18])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 186928567-(Chloromethyl)pentadecane

Product 1

HCID 580983237-(Iodomethyl)pentadecaneYield 84.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

To a reaction vessel, 2.682 g (10.3 mmol) of 2-hexyl-1-chlorodecane, 7.483 g (49.9 mmol, 4.8 eq) of sodium iodide, and 100 mL of acetone were added. The whole was refluxed at 60° C. overnight. The reaction mixture was allowed to reach room temperature, and acetone was removed by evaporation. The residue was extracted with ethyl acetate, and then the organic phase was washed with a saturated brine three times. The organic phase was dried over magnesium sulfate and filtered. The filtrate was concentrated, and the concentrate was dried under vacuum to give 3.075 g (8.73 mmol) of 2-hexyl-1-iododecane as a dark red liquid (crude yield: 85%).

Workup

  1. customto reach room temperature
  2. customacetone was removed by evaporation
  3. extractionThe residue was extracted with ethyl acetate
  4. washthe organic phase was washed with a saturated brine three times
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customthe concentrate was dried under vacuum

Sources & evidence

ORD record
ord-c462a6e8cace4592952ce9ee3aa73810
Source dataset
uspto-grants-2014_07
Patent number
US08773745B2

Reaction notes

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