Sodium Iodide → 2,2-Bis(6-benzyloxyhexyl)ethyl iodide

HRID 1289408Notes

Reaction equation

HRID 1289408 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:16]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-:32].[Na+].CC(=O)CC>O>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:16][I:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6569Methyl Ethyl KetoneHCID 189208332,2-Bis(6-benzyloxyhexyl)ethyl bromide

Product 1

HCID 189208712,2-Bis(6-benzyloxyhexyl)ethyl iodideYield 91.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

First, 6 g of 2,2-bis(6-benzyloxyhexyl)ethyl bromide, 2.19 g of sodium iodide, and 150 ml of 2-butanone were placed in a 300 ml flask. The mixture was stirred under reflux for 16 hours. The reaction mixture was poured into water, and an organic layer was extracted with ether. The ether layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled away. The residue was purified by silica gel column chromatography (eluent: toluene) to obtain 6 g of 2,2-bis(6-benzyloxyhexyl)ethyl iodide (Y: 91.2%). The compound thus obtained had a purity of 95.3% by HPLC.

Workup

  1. temperatureunder reflux for 16 hours
  2. extractionan organic layer was extracted with ether
  3. washThe ether layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled away
  6. customThe residue was purified by silica gel column chromatography (eluent: toluene)

Sources & evidence

ORD record
ord-d5eb4f851bc844469578de3f58a3888c
Source dataset
uspto-grants-1998_05
Patent number
US05750213

Reaction notes

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