Potassium Hydroxide → Dimethyl (2-hydroxyethyl)phosphonate

HRID 1657984Notes

Reaction equation

HRID 1657984 reaction equation
[CH3:1][O:2][P:3]([CH2:7][CH2:8][O:9]C(=O)C)(=[O:6])[O:4][CH3:5].[OH-].[K+]>CO>[CH3:1][O:2][P:3]([CH2:7][CH2:8][OH:9])(=[O:6])[O:4][CH3:5]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 198200Dimethyl (2-acetoxyethyl)phosphonate

Product 1

HCID 2733833Dimethyl (2-hydroxyethyl)phosphonateYield 86.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 50 g of 2-acetoxyethane-phosphonic acid dimethyl ester in 100 ml of anhydrous methanol is mixed with 0.5 g of KOH and heated to 65°-70°C for 5 hours while simultaneously removing a mixture of methyl acetate/methanol by distillation. The crude product is submitted to distillation under reduced pressure, 34 g of 2-hydroxyethane-phosphonic acid dimethyl ester are obtained, corresponding to a yield of 86.5% of the theoretical.

Workup

  1. temperatureheated to 65°-70°C for 5 hours
  2. customwhile simultaneously removing
  3. additiona mixture of methyl acetate/methanol
  4. distillationby distillation
  5. distillationThe crude product is submitted to distillation under reduced pressure, 34 g of 2-hydroxyethane-phosphonic acid dimethyl ester
  6. customare obtained, corresponding to a yield of 86.5% of the theoretical

Sources & evidence

ORD record
ord-fff331fe8afc4575afd6e1a283bbffc9
Source dataset
uspto-grants-1976_06
Patent number
US03962378

Reaction notes

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