Sodium Iodide → Benzene, (8-iodooctyl)-

HRID 22430Notes

Reaction equation

HRID 22430 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I-:16].[Na+]>CC(C)=O>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][I:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 2901511-Chloro-8-phenyloctane

Product 1

HCID 10947018Benzene, (8-iodooctyl)-

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 8-phenyloctyl chloride (4.4 g), sodium iodide (5.34 g) and acetone (20 ml) was heated under reflux for 20 hours. Evaporated, water (20 ml) added and extracted with diethyl ether (20 ml). The extracts were dried, filtered and evaporated to a pale yellow liquid (5.5 g). Distilled to give 8-phenyloctyl iodide, b.p. 200° C. (air bath temperature) at 0.1 mBar.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 20 hours
  3. customEvaporated
  4. additionwater (20 ml) added
  5. extractionextracted with diethyl ether (20 ml)
  6. customThe extracts were dried
  7. filtrationfiltered
  8. customevaporated to a pale yellow liquid (5.5 g)
  9. distillationDistilled

Sources & evidence

ORD record
ord-fcbfdb0afc3740d1a45acd0665c464c3
Source dataset
uspto-grants-1995_06
Patent number
US05428065

Reaction notes

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