Sodium Iodide → 6-Phenyl-1-hexyl iodide

HRID 1603643Notes

Reaction equation

HRID 1603643 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Na+].[I-:15]>CC(C)=O>[I:15][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 561788(6-Bromohexyl)benzene

Product 1

HCID 145296726-Phenyl-1-hexyl iodideYield 99%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

6-Bromo-1-phenylhexane (18.02 g, 0.075 mol) was dissolved in acetone (300 ml), NaI (44.85 g, 0.299 mol) was added, and the mixture heated at reflux temperature for 18 hours. This was filtered and the acetone evaporated under reduced pressure to give a residual mass which was extracted with n-pentane (150 ml). The insoluble solid was filtered off and the filtrate evaporated to give 6-iodo-1-phenylhexane as a colourless liquid (21.22 g, 99%).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux temperature for 18 hours
  3. filtrationThis was filtered
  4. customthe acetone evaporated under reduced pressure
  5. customto give a residual mass which
  6. extractionwas extracted with n-pentane (150 ml)
  7. filtrationThe insoluble solid was filtered off
  8. customthe filtrate evaporated

Sources & evidence

ORD record
ord-e06f8715aa2d445ba818302defc16be9
Source dataset
uspto-grants-1999_11
Patent number
US05990102

Reaction notes

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