Sodium Iodide → 3-Hydroxy-1-iodo-4-octyne

HRID 2420406Notes

Reaction equation

HRID 2420406 reaction equation
[I-:1].[Na+].Cl[CH2:4][CH2:5][CH:6]([OH:12])[C:7]#[C:8][CH2:9][CH2:10][CH3:11]>CC(=O)CC>[OH:12][CH:6]([C:7]#[C:8][CH2:9][CH2:10][CH3:11])[CH2:5][CH2:4][I:1]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 204655481-Chlorooct-4-yn-3-ol

Product 1

HCID 204656213-Hydroxy-1-iodo-4-octyne

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

A mixture of 15 g. of sodium iodide in 100 ml. of 2-butanone is stirred at the reflux temperature for 30 minutes. To the cooled mixture is added 12 g. of 1-chloro-3-hydroxy-4-octyne in 150 ml. of 2-butanone. The resulting mixture is stirred at the reflux temperature for 18 hours then cooled and filtered. The mother liquor is taken to dryness and the residue is triturated with benzene and filtered. The benzene is taken to dryness to give the subject product as an oil. The material is shown to be homogeneous by vapor phase chromatography and thin layer chromatography.

Workup

  1. additionA mixture of 15 g
  2. additionTo the cooled mixture is added 12 g
  3. temperaturethen cooled
  4. filtrationfiltered
  5. customthe residue is triturated with benzene
  6. filtrationfiltered

Sources & evidence

ORD record
ord-caa4990a617d4b148473b6398919b4c1
Source dataset
uspto-grants-1978_08
Patent number
US04110368

Reaction notes

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