Hydrochloric Acid → Diethyl (2-hydroxyethyl)phosphonate

HRID 1657983Notes

Reaction equation

HRID 1657983 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][CH2:10][O:11]C(=O)C)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].Cl.C(OCC(C)C)(=O)C>C(O)C(C)C>[CH2:6]([O:5][P:4]([CH2:9][CH2:10][OH:11])(=[O:8])[O:3][CH2:1][CH3:2])[CH3:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8038Isobutyl AcetateHCID 124696282-(Diethoxyphosphoryl)ethyl acetate

Product 1

HCID 312225Diethyl (2-hydroxyethyl)phosphonateYield 62.8%

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent2×

Procedure

100 g of 2-acetoxyethane phosphonic acid diethyl ester are blended with 200 ml of isobutyl alcohol containing 2 g of HCl and heated to 120°-150°C for 5 hours. A mixture of isobutyl acetate and isobutanol is removed continuously by distillation in the course of the reaction. By gas chromatography of the mixture of isobutyl acetate/isobutanol, no ethyl acetate and only traces of ethanol were found. 51 g of 2-hydroxyethane-phosphonic acid diethyl ester are obtained after distillation under reduced pressure, corresponding to a yield of 62% of the theoretical.

Workup

  1. temperatureheated to 120°-150°C for 5 hours
  2. customis removed continuously by distillation in the course of the reaction
  3. additionBy gas chromatography of the mixture of isobutyl acetate/isobutanol

Sources & evidence

ORD record
ord-a51f0caa8ea7418bbc737e15926b8502
Source dataset
uspto-grants-1976_06
Patent number
US03962378

Reaction notes

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