Methyl iodide → HCID 85817054, compound

HRID 48922Notes

Reaction equation

HRID 48922 reaction equation
[CH3:1][N:2]([CH3:13])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([OH:12])[CH:5]=1.[CH3:14][I:15]>O1CCOCC1>[I-:15].[CH3:13][N+:2]([CH3:14])([CH3:1])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([OH:12])[CH:5]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 13434502Dimethyl(3-hydroxy-4-methoxybenzyl)amine

Product 1

HCID 85817054HCID 85817054, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a dioxane solution (250 ml) of the dimethyl(3-hydroxy-4-methoxybenzyl)amine thus obtained (16 g, 88.5 mmol) was added methyl iodide (8.26 ml, 132 mmol) and the resulting mixture was refluxed for 4 h. The solid formed was filtered and washed with dioxane to yield 23 g (81%) of the trimethyl(3-hydroxy-4-methoxybenzyl) ammonium iodide salt. This latter was suspended in 100 ml xylene, triethyl phosphite (18 ml, 107 mmol) was added and the resulting mixture was refluxed for 16 h. The solid formed was filtered and the solvent and excess of phosphite were evaporated under vacuum to give after short path distillation diethyl (3-hydroxy-4-methoxybenzyl)phosphonate as a viscous oil (4 g, 10%).

Workup

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

Sources & evidence

ORD record
ord-57b5a3c0bde84ebdb42b726e30e516f4
Source dataset
uspto-grants-2004_03
Patent number
US06706698B2

Reaction notes

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