Methyl iodide → Diethyl methylphosphonate

HRID 1684268Notes

Reaction equation

HRID 1684268 reaction equation
[CH3:1]I.[P:3]([O:10]CC)([O:7][CH2:8][CH3:9])[O:4][CH2:5][CH3:6]>>[CH3:1][P:3](=[O:10])([O:7][CH2:8][CH3:9])[O:4][CH2:5][CH3:6]

Participants

3

Reactant 2

HCID 6328Methyl iodideHCID 31215Triethyl phosphite

Product 1

HCID 12685Diethyl methylphosphonate

Conditions

Temperature
-10 °C

Procedure

188 g (1.32 mol) of methyl iodide are poured under nitrogen into a dry three-necked flask surmounted by an alcohol condenser (-10° C.), and then heated to the refluxing temperature. 168 g (1.02 mol) of triethyl phosphite are then added dropwise. The reaction is exothermic, and the temperature rises in the course of one hour to 73° C. The temperature of the mixture is maintained for one hour at between 70° and 75° C., and the solution is then cooled and concentrated in a rotary evaporator. The diethyl methylphosphonate is distilled under nitrogen, under reduced pressure.

Workup

  1. customsurmounted by an alcohol condenser
  2. temperatureThe temperature of the mixture is maintained for one hour at between 70° and 75° C.
  3. temperaturethe solution is then cooled
  4. concentrationconcentrated in a rotary evaporator
  5. distillationThe diethyl methylphosphonate is distilled under nitrogen, under reduced pressure

Sources & evidence

ORD record
ord-0b06ddf898d84c60a58fbee59e4ddfb2
Source dataset
uspto-grants-1997_06
Patent number
US05639902

Reaction notes

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