Di-tert-butyl peroxide → diethyl isobutylphosphonate

HRID 437047Notes

Reaction equation

HRID 437047 reaction equation
[CH2:1]([O:3][P:4]([O-:8])[O:5][CH2:6][CH3:7])[CH3:2].[CH2:9]=[C:10]([CH3:12])[CH3:11].C(OOC(C)(C)C)(C)(C)C>>[CH2:1]([O:3][P:4]([CH2:9][CH:10]([CH3:12])[CH3:11])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

4

Reactant 3

HCID 8033Di-tert-butyl peroxideHCID 8255IsobutyleneHCID 3780918Diethylphosphite2×

Product 1

HCID 638729diethyl isobutylphosphonateYield 81%

Conditions

Temperature
-80 °C

Procedure

In a 10-liter flask with stirrer, internal thermometer, reflux condenser (-80° C.) and a cooled dropping funnel, 2070 g of diethylphosphite is heated to 150° C. Then over a period of about 90 minutes a mixture of 2070 g of diethylphosphite, 1680 g of isobutene and 44 g of ditertiarybutyl peroxide is added drop by drop. The reaction heat that develops is removed by external cooling. Then heating at 150° C. continues for about 30 minutes. Vacuum distillation through a 12-tray column delivers an 81% yield of pure product.

Workup

  1. additionis added drop by drop
  2. temperatureThe reaction heat that
  3. customdevelops is removed by external cooling
  4. temperatureThen heating at 150° C.
  5. distillationVacuum distillation through a 12-tray column

Sources & evidence

ORD record
ord-7d951f3f3c6644098e68d6818351f03c
Source dataset
uspto-grants-1977_06
Patent number
US04029679

Reaction notes

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