p-Toluenesulfonic acid → Dimethyl (2-hydroxyethyl)phosphonate

HRID 1657987Notes

Reaction equation

HRID 1657987 reaction equation
[CH3:1][O:2][P:3]([CH2:7][CH2:8][O:9]C(=O)C)(=[O:6])[O:4][CH3:5].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:1][O:2][P:3]([CH2:7][CH2:8][OH:9])(=[O:6])[O:4][CH3:5]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 198200Dimethyl (2-acetoxyethyl)phosphonate

Product 1

HCID 2733833Dimethyl (2-hydroxyethyl)phosphonateYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 100 g of 2-acetoxyethane-phosphonic acid dimethyl ester in 100 ml of anhydrous methanol -- 4 g of p-toluenesulfonic acid being added -- is heated for 5 hours to 65°-75°C while removing simultaneously by distillation a mixture of methyl acetate/methanol. After distillation under reduced pressure, 59 g of 2-hydroxyethane-phosphonic acid dimethyl ester are obtained, corresponding to a yield of 75% of the theoretical.

Workup

  1. temperatureis heated for 5 hours to 65°-75°C
  2. customwhile removing simultaneously by distillation
  3. additiona mixture of methyl acetate/methanol
  4. distillationAfter distillation under reduced pressure, 59 g of 2-hydroxyethane-phosphonic acid dimethyl ester
  5. customare obtained, corresponding to a yield of 75% of the theoretical

Sources & evidence

ORD record
ord-51e0fd4ec90141e8b8843f4f32d4971e
Source dataset
uspto-grants-1976_06
Patent number
US03962378

Reaction notes

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