Sodium Iodide → p-Benzyloxybenzyl iodide

HRID 2394080Notes

Reaction equation

HRID 2394080 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13]Cl)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-:17].[Na+]>CC(C)=O>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][I:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 700424-Benzyloxybenzyl chloride

Product 1

HCID 11723738p-Benzyloxybenzyl iodide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 1.0 g (4.3 mmol) of 4-benzyloxybenzyl chloride (Fluka; Buchs/Switzerland) in 8 ml of acetone is stirred at RT with 3.13 g (20.9 mmol) of sodium iodide. After 90 min, a gas chromatogram of the reaction mixture indicates that the reaction is complete; the reaction mixture is therefore poured onto ether, and this mixture is washed with 10% sodium thiosulfate solution and saline. Drying the organic phase with Na2 SO4, and evaporating, yields the title compound: 1H-NMR (200 MHz, CDCl3 : 4.48 (s, 2H), 5.06 (s, 2H), 6.85-6.95 (m, 2H), 7.25-7.48 (m, 7H).

Workup

  1. additionthe reaction mixture is therefore poured onto ether
  2. washthis mixture is washed with 10% sodium thiosulfate solution and saline
  3. customDrying the organic phase with Na2 SO4
  4. customevaporating

Sources & evidence

ORD record
ord-47f9c073449b4d37a266b5a3d6ac5672
Source dataset
uspto-grants-1998_09
Patent number
US05807891

Reaction notes

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