Dimethyl (2-acetoxyethyl)phosphonate → Dimethyl (2-hydroxyethyl)phosphonate

HRID 1657980Notes

Reaction equation

HRID 1657980 reaction equation
[CH3:1][O:2][P:3]([CH2:7][CH2:8][O:9]C(=O)C)(=[O:6])[O:4][CH3:5].[Na].C(OC)(=O)C.CO>CO>[CH3:1][O:2][P:3]([CH2:7][CH2:8][OH:9])(=[O:6])[O:4][CH3:5]

Participants

5

Reactant 3

HCID 198200Dimethyl (2-acetoxyethyl)phosphonateHCID 5360545SodiumHCID 11389366Methyl acetate methanol

Product 1

HCID 2733833Dimethyl (2-hydroxyethyl)phosphonateYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

600 g of 2-acetoxyethane-phosphonic acid dimethyl ester are heated for 5 hours to 65°-75°C in 600 ml of methanol to which 3 g of sodium had been added. A mixture of methyl acetate/methanol is removed continuously by distillation. The reaction being terminated, the residue is submitted to distillation under reduced pressure, 369 g of 2-hydroxyethane-phosphonic acid dimethyl ester (boiling point: 122°C/0.2 torr) are obtained, corresponding to a yield of 84% in the theoretical.

Workup

  1. additionhad been added
  2. customis removed continuously by distillation
  3. customThe reaction being terminated
  4. distillationthe residue is submitted to distillation under reduced pressure, 369 g of 2-hydroxyethane-phosphonic acid dimethyl ester (boiling point: 122°C/0.2 torr)
  5. customare obtained, corresponding to a yield of 84% in the theoretical

Sources & evidence

ORD record
ord-512a85c7d6684c5aa1aef9f59ba491d3
Source dataset
uspto-grants-1976_06
Patent number
US03962378

Reaction notes

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