Ethyl orthoformate → Diethyl diethoxymethylphosphonate

HRID 1899801Notes

Reaction equation

HRID 1899801 reaction equation
[CH:1]([O:8][CH2:9][CH3:10])([O:5][CH2:6][CH3:7])OCC.[P:11]([O:18]Cl)([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14]>>[CH2:13]([O:12][P:11]([CH:1]([O:5][CH2:6][CH3:7])[O:8][CH2:9][CH3:10])(=[O:18])[O:15][CH2:16][CH3:17])[CH3:14]

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 21961456HCID 21961456, compound

Product 1

HCID 4488725Diethyl diethoxymethylphosphonateYield 83.3%

Conditions

Temperature
135 °C

Procedure

To a flask containing triethyl orthoformate (23.6 gm; 0.16 mole) equipped with a magnetic stirrer, condensor, and nitrogen atmosphere, is added diethyl chloro phosphite (25 gm; 0.16 mole) over 15-30 minutes and an extremely exothermic reaction occurs. The reaction solution is then heated at 135° C. for 3 hours. The resulting solution is distilled using a Kugelrohr distillation apparatus at 80° C. (0.01 mm Hg) to yield 32 gm of diethoxymethylphosphonic acid diethyl ester (31P NMR 13.2 ppm).

Workup

  1. customequipped with a magnetic stirrer
  2. customan extremely exothermic reaction
  3. distillationThe resulting solution is distilled
  4. distillationa Kugelrohr distillation apparatus at 80° C. (0.01 mm Hg)

Sources & evidence

ORD record
ord-76cbda39f000482a8c11a9c32ad19b74
Source dataset
uspto-grants-1996_11
Patent number
US05574024

Reaction notes

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