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ChemicalBook CAS DataBase List Trimethyl phosphonoacetate
5927-18-4

Trimethyl phosphonoacetate synthesis

5synthesis methods
The trimethyl phosphonoacetate is prepared from trimethyl phosphite and methyl chloroacetate through Michael Arbuzov rearrangement reaction. The synthetic method satisfies the chemical equations that CH2ClCOOH + CH3OH → CH5ClO2 + H2O, CH5ClO2 + C3H9O3P → C5H11O5P + CH3Cl.
-

Yield:-

Reaction Conditions:

with potassium carbonate at 20 - 30;

Steps:

Synthesis of the composition
Methyl chloroacetate, 35.8 g (29.0 mL, 330 mmol), was added dropwise with vigorous stirring at 20-30° to a mixture of 36.6 g (30.4 mL, 330 mmol) of dimethyl phosphite and 91.0 g (660 mmol) of powdered K2CO3. The reaction mixture was stirred at 20-30° for 18 h, diluted with 50 mL of water, heated under reflux for 4 h, and let to cool down to room temperature. Concentrated HCl, 85 mL (990 mmol) , was then added with stirring, and the mixture was boiled for 6 h with distilletion of the water-metanol fraction up to bp 90°. The still residue at 20-30° was neutralized with 40% aqueous solution of 35.3 g (630 mmol) of KOH to 8, the mixture was stirred for 1 h at room temperature, and the precipitate of KCl that formed was filtered off to obtain 215.8 g of aqueous solution of di- and trisalts of [hydroxy(methoxy)phosphinoyl]-acetic (4) and phosphonoacetic (7, 8) acids (21% per phosphonoacetic acid, ratio 1 : 2), as well as phosphoric acid (1.6% per phosphoric acid) and KCl.

References:

Alimbarova;Kharlamov;Bondarenko;Barinskii [Russian Journal of General Chemistry,2015,vol. 85,# 10,p. 2441 - 2448][Ross. Khim. Zh.,2014,vol. 58,# 1,p. 23 - 30,8]

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