Sulfuric Acid → Diethyl (2-hydroxyethyl)phosphonate

HRID 1657986Notes

Reaction equation

HRID 1657986 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].OS(O)(=O)=O>C(O)C>[CH2:6]([O:5][P:4]([CH2:9][CH2:10][OH:11])(=[O:8])[O:3][CH2:1][CH3:2])[CH3:7]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 124696282-(Diethoxyphosphoryl)ethyl acetate

Product 1

HCID 312225Diethyl (2-hydroxyethyl)phosphonateYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

100 g of 2-acetoxyethane phosphonic acid diethyl ester are heated to 80°C jointly with 200 ml of ethanol. To this solution are added dropwise within 5 hours 20 ml of ethanol containing 1 wt.% of H2SO4 while simultaneously removing by continuous distillation a mixture of ethylacetate and ethanol. The residue is submitted to distillation under reduced pressure. 64 g of 2-hydroxyethane-phosphonic acid diethyl ester are obtained, corresponding to a yield of 80% of the theoretical.

Workup

  1. customwhile simultaneously removing by continuous distillation
  2. additiona mixture of ethylacetate and ethanol
  3. distillationThe residue is submitted to distillation under reduced pressure

Sources & evidence

ORD record
ord-693111acb26648e3a0c340ae159facb7
Source dataset
uspto-grants-1976_06
Patent number
US03962378

Reaction notes

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