Ethanol → Phosphonic acid, (dichloromethyl)-, diethyl ester

HRID 66547Notes

Reaction equation

HRID 66547 reaction equation
[CH3:1][CH2:2][O-:3].[Na+].[Cl:5][CH:6]([Cl:11])[P:7](Cl)(Cl)=[O:8].[CH2:12]([OH:14])[CH3:13]>C1(C)C=CC=CC=1>[CH2:2]([O:3][P:7]([CH:6]([Cl:11])[Cl:5])(=[O:8])[O:14][CH2:12][CH3:13])[CH3:1]

Participants

5

Reactant 3

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 3538911(Dichloromethyl)phosphonic dichloride

Product 1

HCID 11085347Phosphonic acid, (dichloromethyl)-, diethyl esterYield 78%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
20 °C

Procedure

153.5 g (2.26 mol) of sodium ethylate in 800 ml of ethanol were added dropwise, at 5°-10° C., to a solution of 227.5 g (1.13 mol) of dichloromethane-phosphonic acid dichloride in 800 ml of toluene. The mixture was subsequently stirred at 20° C. for 5 hours. It was then filtered, the filtrate was concentrated and the residue was subjected to fractional distillation. 195 g (78% of theory) of dichloromethane-phosphonic acid diethyl ester were obtained in the form of a colorless oil of boiling point 84° C./1 mbar.

Workup

  1. filtrationIt was then filtered
  2. concentrationthe filtrate was concentrated
  3. distillationthe residue was subjected to fractional distillation

Sources & evidence

ORD record
ord-3c85e1ad95134b908dc6b3dfd0c04f1f
Source dataset
uspto-grants-1982_08
Patent number
US04342704

Reaction notes

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