Hydrochloric Acid → Diethyl (2-hydroxyethyl)phosphonate

HRID 1657982Notes

Reaction equation

HRID 1657982 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(OC)(=O)C.CO>CO>[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 11389366Methyl acetate methanolHCID 124696282-(Diethoxyphosphoryl)ethyl acetate

Product 1

HCID 312225Diethyl (2-hydroxyethyl)phosphonateYield 83.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

100 g of 2-acetoxyethane phosphonic acid diethyl ester are blended with 200 ml of methanol containing 1 wt.% of HCl and heated to 65°-70°C for 4 hours. A mixture of methyl acetate/methanol is removed continuously from the reaction mixture by distillation. Upon submitting the mixture of methyl acetate/methanol to gas chromatography no ethyl acetate at all and only traces of ethanol are found. The crude 2-hydroxyethanephosphonic acid diethyl ester is distilled under reduced pressure. 68 g of 2-hydroxyethane-phosphonic acid diethyl ester (b.p. 106°-109°C/0.1 torr) are obtained, corresponding to a yield of 83.5% of the theoretical.

Workup

  1. temperatureheated to 65°-70°C for 4 hours
  2. customis removed continuously from the reaction mixture by distillation
  3. additionthe mixture of methyl acetate/methanol to gas chromatography no ethyl acetate at all and only traces of ethanol
  4. distillationThe crude 2-hydroxyethanephosphonic acid diethyl ester is distilled under reduced pressure

Sources & evidence

ORD record
ord-2d388bf236aa4ef99ada775a1009db1a
Source dataset
uspto-grants-1976_06
Patent number
US03962378

Reaction notes

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