Sodium Iodide → 8-Iodo-1-octyne

HRID 840054

Reaction equation

HRID 840054 reaction equation
[CH2:1](OS(C1C=CC(C)=CC=1)(=O)=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]#[CH:8].[I-:20].[Na+]>CC(C)=O>[I:20][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]#[CH:8]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 10779145Oct-7-yn-1-yl 4-methylbenzene-1-sulfonate

Product 1

HCID 226215568-Iodo-1-octyneYield 94.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 7-octynyl-p-toluenesulfonate (18.3 g, 65.2 mmol), sodium iodide (9.77 g, 65.2 mmol) and acetone (91 ml) was allowed to react for four hours under reflux. After cooling, the precipitates were removed by filtration, and the filtrate was concentrated. The resulting residue was purified by silica gel column chromatography (eluent; hexane) to afford 14.5 g of 8-iodo-1-octyne (yield; 94.2%).

Workup

  1. customto react for four hours
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. customthe precipitates were removed by filtration
  5. concentrationthe filtrate was concentrated
  6. customThe resulting residue was purified by silica gel column chromatography (eluent; hexane)

Sources & evidence

ORD record
ord-15557948ec354671bcc50160cab9f5a5
Source dataset
uspto-grants-2002_04
Patent number
US06365350B1

Linked notes

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