Reaction #95547

Reaction equation

trimethyl phosphite

2-iodomethyl-3-iodopropene

trimethyl phosphite

→

title compound

Yield 92.0%

1,3-bis(dimethylphosphono)-2-methylene-propane

Yield 92.0%

Solvents

benzene

Conditions

Workup

1. 1
   Otherequipped with an addition funnel, a gas inlet tube
2. 2
   workup.DISTILLATIONa Vigreux column with distilling head
3. 3
   TemperatureThe phosphite was heated
4. 4
   Temperatureat reflux
5. 5
   Otherto collect
6. 6
   workup.DISTILLATIONDistillation of the reaction mixture

Procedure

400 ml of trimethyl phosphite was placed into a 2-1 flask equipped with an addition funnel, a gas inlet tube, and a Vigreux column with distilling head. The phosphite was heated at reflux, then a solution of 131 g (0.425 Mole) of 2-iodomethyl-3-iodopropene [see J.Amer.Chem.Soc., 89, 4688 (1967)] in 200 ml of benzene was added dropwise over a period of 2 h, followed by an additional 100 ml of trimethyl phosphite within 30 min. The reaction was run under nitrogen, and approx. 150 ml of distillate was allowed to collect. Distillation of the reaction mixture afforded 106 g (92%) of the title compound, b.p. 125°-7°/0.08 Torr;

Source