Sodium Iodide → Benzyl iodide

HRID 971916Notes

Reaction equation

HRID 971916 reaction equation
[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-:9].[Na+].[CH3:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][C:17]=1[CH2:18][CH2:19][CH3:20]>CC(C)=O>[CH2:1]([I:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-:9].[CH2:1]([N+:14]1[CH:15]=[CH:16][C:17]([CH2:18][CH2:19][CH3:20])=[C:12]([CH3:11])[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 7503Benzyl ChlorideHCID 45943243-methyl-4-propyl-pyridine

Product 2

HCID 12098Benzyl iodideHCID 21312547HCID 21312547, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of benzyl iodide in acetone was prepared from benzyl chloride (823 g.) and sodium iodide (975 g.). 3-Methyl-4-propylpyridine (879 g.) was added and the mixture was stirred at room temperature. Crystallization of the product from acetone-isopropyl acetate afforded 1-benzyl-3-methyl-4-propylpyridinium iodide in two crops (1334 g. and 162 g.), which melted at 94°-95° C.

Workup

  1. customCrystallization of the product from acetone-isopropyl acetate

Sources & evidence

ORD record
ord-8a3222ccce7246efb610d9c45780149c
Source dataset
uspto-grants-1979_07
Patent number
US04161598

Reaction notes

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