Sodium Iodide → p-Methoxybenzyl iodide

HRID 1585318Notes

Reaction equation

HRID 1585318 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, at RT, together with 9.4 g (62.6 mmol) of sodium iodide. A gas chromatogram of the reaction mixture, carried out after 90 min, 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 Na2SO4, and evaporating it, affords the title compound: 1H-NMR (200 MHz, CD3OD: 3.78 (s, 3H), 4.54 (s, 2H), 6.8-6.95 and 7.2-7.4 (2m, each 2H).

Workup

  1. additionthe reaction mixture is therefore poured onto ether
  2. washthis mixture is washed with 10% sodium thiosulfate solution and saline
  3. dry with materialDrying the organic phase with Na2SO4
  4. customevaporating it

Sources & evidence

ORD record
ord-bda4056047b04c399749e516d187e1b1
Source dataset
uspto-grants-1999_08
Patent number
US05935976

Reaction notes

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