Sodium Iodide → HCID 21317518, compound

HRID 328764Notes

Reaction equation

HRID 328764 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH:5]([O:11][C:12](=[O:14])[CH3:13])[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[I-:15].[Na+]>CC(C)=O>[I:15][CH2:2][CH2:3][CH2:4][CH:5]([O:11][C:12](=[O:14])[CH3:13])[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 131047161-Chloro-4-acetoxynonane

Product 1

HCID 21317518HCID 21317518, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1-chloro-4-acetoxynonane (Ex. 1, Step B-3) (35.3 g., 0.16 mole) and sodium iodide (120 g., 0.8 mole) in acetone (350 ml.) is stirred and heated at reflux with exclusion of light for 10 hours. The resulting suspension is filtered and the collected sodium chloride washed with acetone. The combined filtrate and washings are evaporated in vacuo leaving a residual mass which is partitioned between ether and water. The organic extract is washed with dilute aqueous sodium thiosulfate and water, dried over sodium sulfate and evaporated in vacuo providing the title compound as a colorless liquid (48.7 g., 98%), pmr (CDCl3) δ 2.0 (s, 3H), 3.18 (t, 2H) and 4.98 (m, H).

Workup

  1. temperatureheated
  2. temperatureat reflux with exclusion of light for 10 hours
  3. filtrationThe resulting suspension is filtered
  4. washthe collected sodium chloride washed with acetone
  5. customThe combined filtrate and washings are evaporated in vacuo
  6. customleaving a residual mass which
  7. customis partitioned between ether and water
  8. extractionThe organic extract
  9. washis washed with dilute aqueous sodium thiosulfate and water
  10. dry with materialdried over sodium sulfate
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-6bc823adb9dc4e04a430467a72d41239
Source dataset
uspto-grants-1977_04
Patent number
US04018802

Reaction notes

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