Reaction #77201

Reaction equation

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

trimethyl phosphite

→

dimethyl (4-hydroxy-3-methoxy-5-methylbenzyl)phosphonate

Yield 83.0%

Solvents

xylene

Conditions

Workup

1. 1
   Temperaturethe resulting mixture was refluxed for 14 h
2. 2
   OtherThe solid formed
3. 3
   Filtrationwas filtered
4. 4
   Otherthe solvent and excess of phosphite were evaporated under vacuum

Procedure

Trimethyl(4-hydroxy-3-methoxy-5-methylbenzyl)ammonium iodide (1 g, 3.0 mmol) was suspended in 8 ml xylene, trimethyl phosphite (0.52 ml, 4.4 mmol) was added dropwise and the resulting mixture was refluxed for 14 h. The solid formed was filtered and the solvent and excess of phosphite were evaporated under vacuum to yield dimethyl (4-hydroxy-3-methoxy-5-methylbenzyl)phosphonate as a viscous oil (0.64 g, 83%).

Source