Sodium Iodide → 6-Phenyl-1-hexyl iodide

HRID 863840Notes

Reaction equation

HRID 863840 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=O)=O.[I-:18].[Na+]>CC(C)=O>[C:12]1([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][I:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 130797026-Phenylhex-1-yl methylsulfonate

Product 1

HCID 145296726-Phenyl-1-hexyl iodide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 6-phenylhex-1-yl methylsulfonate (4.55 g; 17.3 mmol) dissolved in acetone (100 ml) is added sodium iodide (2.5 g; 173 mmol) and the reaction mixture is heated 2 hours at reflux. The reaction mixture is then concentrated to dryness and partitioned between ether and water. The organic phase is separated, dried, concentrated to dryness and purified with silica chromatography using 10 EtOAc/90 petroleum ether to give 6-phenyl-1-hexyl iodide as a colorless oil which is used directly in Step F.

Workup

  1. temperaturethe reaction mixture is heated 2 hours
  2. temperatureat reflux
  3. concentrationThe reaction mixture is then concentrated to dryness
  4. custompartitioned between ether and water
  5. customThe organic phase is separated
  6. customdried
  7. concentrationconcentrated to dryness
  8. custompurified with silica chromatography

Sources & evidence

ORD record
ord-8f17090b939c4349a5cc3b771a243771
Source dataset
uspto-grants-1996_10
Patent number
US05561143

Reaction notes

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