Trimethyl phosphite → 1,3-Bis(dimethylphosphono)-2-methylene-propane

HRID 67269Notes

Reaction equation

HRID 67269 reaction equation
[P:1]([O:6]C)([O:4][CH3:5])[O:2][CH3:3].I[CH2:9][C:10]([CH2:12]I)=[CH2:11]>C1C=CC=CC=1>[CH3:3][O:2][P:1]([CH2:9][C:10](=[CH2:11])[CH2:12][P:1]([O:2][CH3:3])([O:4][CH3:5])=[O:6])([O:4][CH3:5])=[O:6]

Participants

4

Reactant 2

HCID 8472Trimethyl phosphite2×HCID 110450293-Iodo-2-(iodomethyl)prop-1-ene

Product 1

HCID 205268441,3-Bis(dimethylphosphono)-2-methylene-propaneYield 92%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

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;

Workup

  1. customequipped with an addition funnel, a gas inlet tube
  2. distillationa Vigreux column with distilling head
  3. temperatureThe phosphite was heated
  4. temperatureat reflux
  5. customto collect
  6. distillationDistillation of the reaction mixture

Sources & evidence

ORD record
ord-68c07a8e9c60486885b3dfcde221822a
Source dataset
uspto-grants-1982_08
Patent number
US04346023

Reaction notes

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