Sodium Iodide → HCID 10407167, compound

HRID 1995272Notes

Reaction equation

HRID 1995272 reaction equation
C(OCC)(=O)C.[CH2:7](O)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]/[CH:15]=[CH:16]\[CH2:17]/[CH:18]=[CH:19]\[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].S(C1C=CC(C)=CC=1)([O-])(=O)=O.[I-:37].[Na+]>CC(C)=O>[CH2:7]([I:37])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]/[CH:15]=[CH:16]\[CH2:17]/[CH:18]=[CH:19]\[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8857Ethyl AcetateHCID 85570p-ToluenesulfonateHCID 5365682Linoleyl alcohol

Product 1

HCID 10407167HCID 10407167, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of linoleyl alcohol (5.32 g, 200 mmole) and pyridine (40 ml) was cooled to 0° C. and added to p-toluene-sulfonic chloride (4.2 g, 220 mmole) in 10 ml of pyridine. The resulting solution was stirred overnight at 0° C. and poured into 50 ml of ice water. The organic layer was extracted with 100 ml of ether and the organic layer was washed with 1% aqueous hydrochloric acid until acidic and then washed three times with water. The organic solution was dried over magnesium sulfate, filtered and the solvent evaporated to give 6 g of oily material having an Rf of 0.3 on thin layer chromatography (20Δ ethyl acetate/Skelly B linoleyl alcohol Rf =0.1). To the crude tosylate (6 g, 140 mmole) was added acetone (150 ml) and sodium iodide (300 mmole, 4.5 g), and the mixture was heated gently on a steam bath for 3 hours. The solvent was removed in vacuo and 200 ml of ether added thereto. The organic layer was washed twice with an aqueous solution of sodium bisulfite, twice with water and dried over magnesium sulfate, filtered and solvent removed. The crude iodide was purified by column chromatography over silica gel and eluted with Skelly B to yield 5.2 g of linoleyl iodide Rf ethyl acetate--Skelly B (10:90 v/v)=0.7 of formula II of Chart A.

Workup

  1. temperaturethe mixture was heated gently on a steam bath for 3 hours
  2. customThe solvent was removed in vacuo and 200 ml of ether
  3. additionadded
  4. washThe organic layer was washed twice with an aqueous solution of sodium bisulfite, twice with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customsolvent removed
  8. customThe crude iodide was purified by column chromatography over silica gel
  9. washeluted with Skelly B

Sources & evidence

ORD record
ord-ca9c9ae9ea1548f0830db8f4ab0fb203
Source dataset
uspto-grants-1983_09
Patent number
US04404144

Reaction notes

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