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

HRID 1112671Notes

Reaction equation

HRID 1112671 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 and 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. temperaturecooled
  4. filtrationfiltered
  5. customthe residue is triturated with benzene
  6. filtrationfiltered

Sources & evidence

ORD record
ord-c3743e62b38b4bd8871c094466628842
Source dataset
uspto-grants-1978_10
Patent number
US04123456

Reaction notes

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