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

HRID 1657985Notes

Reaction equation

HRID 1657985 reaction equation
[CH3:1][O:2][P:3]([CH2:7][CH2:8][O:9]C(=O)C)(=[O:6])[O:4][CH3:5].C(OC)(=O)C.CO>CO.S(=O)(=O)(O)O>[CH3:1][O:2][P:3]([CH2:7][CH2:8][OH:9])(=[O:6])[O:4][CH3:5]

Participants

5

Reactant 2

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

Product 1

HCID 2733833Dimethyl (2-hydroxyethyl)phosphonateYield 85%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 887MethanolSolvent

Procedure

A solution of 50 g of 2-acetoxyethane phosphonic acid dimethyl ester in 100 ml of anhydrous methanol is heated to 65°-70°C for 5 hours, while adding one drop of concentrated sulfuric acid. A mixture of methyl acetate/methanol is removed continuously by distillation in the course of the reaction. After a distillation under reduced pressure 33.5 g of 2-hydroxyethane-phosphonic acid dimethyl ester are obtained, corresponding to a yield of 85% of the theoretical.

Workup

  1. customis removed continuously by distillation in the course of the reaction
  2. distillationAfter a distillation under reduced pressure 33.5 g of 2-hydroxyethane-phosphonic acid dimethyl ester
  3. customare obtained, corresponding to a yield of 85% of the theoretical

Sources & evidence

ORD record
ord-8e4bed0d007c4dacb9952df7302ab66c
Source dataset
uspto-grants-1976_06
Patent number
US03962378

Reaction notes

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