Methyl iodide → HCID 85817054, compound

Participants

Reaction Steps

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%).

Provenance & Evidence