Sodium Iodide → p-Methoxybenzyl iodide

HRID 1376658Notes

Reaction equation

HRID 1376658 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Cl)=[CH:5][CH:4]=1.[I-:11].[Na+]>CC(C)=O>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][I:11])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 11746977p-Methoxybenzyl iodide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 1.7 ml (12.8 mmol) of 4-methoxybenzyl chloride (Fluka; Buchs/Switzerland) in 25 ml of acetone is stirred with 9.4 g (62.6 mmol) of sodium iodide at room temperature. Gas chromatography of the reaction mixture after 90 minutes indicates that the reaction is complete, and the reaction mixture is therefore poured onto ether and washed with 10% sodium thiosulfate solution and brine. Drying of the organic phase with Na2SO4 and concentration by evaporation yield the title compound; 1H-NMR (200 MHz, CD3OD: 3.78 (s, 3 H), 4.54 (s, 2 H), 6.8-6.95 and 7.2-7.4 (2m, each 2 H).

Workup

  1. additionthe reaction mixture is therefore poured onto ether
  2. washwashed with 10% sodium thiosulfate solution and brine
  3. dry with materialDrying of the organic phase with Na2SO4 and concentration by evaporation

Sources & evidence

ORD record
ord-4d4e836890214ef88bc0950aac5526ee
Source dataset
uspto-grants-1997_09
Patent number
US05663168

Reaction notes

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