Sodium Iodide → HCID 10894686, compound

HRID 726489Notes

Reaction equation

HRID 726489 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[I-:22].[Na+]>CC(C)=O>[I:22][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 11100339Benzene, [[(12-bromododecyl)oxy]methyl]-

Product 1

HCID 10894686HCID 10894686, compoundYield 104.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

First, 12.4 g of 1-bromo-12-benzyloxydodecane, 6.3 g of sodium iodide, and 125 ml of acetone were placed in a 200 ml flask whose content was replaced with argon. Then, the mixture was stirred under reflux for 5 hours. An insoluble matter was filtered away and a filtrate was concentrated. Thereafter, ether was introduced into the residue. The ether layer was washed with water and dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled away. The residue was purified by silica gel column chromatography (eluent: toluene/hexane=1/1) to obtain 14.7 g of 1-iodo-12-benzyloxydodecane (Y: 100%). The compound thus obtained had a purity of 96.1% by GC.

Workup

  1. temperatureunder reflux for 5 hours
  2. filtrationAn insoluble matter was filtered away
  3. concentrationa filtrate was concentrated
  4. additionThereafter, ether was introduced into the residue
  5. washThe ether layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThereafter, the solvent was distilled away
  8. customThe residue was purified by silica gel column chromatography (eluent: toluene/hexane=1/1)

Sources & evidence

ORD record
ord-eca8047c1beb42378e71efc407e95bdc
Source dataset
uspto-grants-1998_01
Patent number
US05709911

Reaction notes

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