Methyl iodide → Trimethyl(4-hydroxy-3-methoxy-5-methylbenzyl)ammonium iodide

HRID 48920Notes

Reaction equation

HRID 48920 reaction equation
[CH3:1][N:2]([CH3:14])[CH2:3][C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([OH:11])=[C:6]([O:12][CH3:13])[CH:5]=1.[CH3:15][I:16]>O1CCOCC1>[I-:16].[CH3:14][N+:2]([CH3:15])([CH3:1])[CH2:3][C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([OH:11])=[C:6]([O:12][CH3:13])[CH:5]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 10382346HCID 10382346, compound

Product 1

HCID 20634507Trimethyl(4-hydroxy-3-methoxy-5-methylbenzyl)ammonium iodideYield 98%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a dioxane solution (600 ml) of dimethyl(4-hydroxy-3-methoxy-5-methylbenzyl)amine (98 g, 0.50 mol) was added methyl iodide (69 ml, 1.11 mol) and the resulting mixture was refluxed for 2 h. The solid formed was filtered and washed with dioxane to yield 165 g (98%) of the trimethyl(4-hydroxy-3-methoxy-5-methylbenzyl)ammonium iodide salt.

Workup

  1. temperaturethe resulting mixture was refluxed for 2 h
  2. customThe solid formed
  3. filtrationwas filtered
  4. washwashed with dioxane

Sources & evidence

ORD record
ord-6362949ddcbb42adb9ac3daf20f78de4
Source dataset
uspto-grants-2004_03
Patent number
US06706698B2

Reaction notes

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