Preparation method of 3-(methyl alkoxy phosphoryl) propionic acid ester compound

A technology of methyl alkoxyphosphoryl and methyl dialkyl phosphite, which is applied in the field of preparation of 3-propionate compounds, can solve the problems of cumbersome operation, large amount of three wastes, and unfavorable industrial production, etc. question

Inactive Publication Date: 2010-03-10
LIER CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The product (I') yield of this reaction is relatively low, only 81.4%, and after the reaction is completed, the separation of catalyst, by-product and product is required, the operation is loaded down with trivial details, and the three wastes produced in the reaction process are more
Not conducive to industrial production

Method used

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  • Preparation method of 3-(methyl alkoxy phosphoryl) propionic acid ester compound
  • Preparation method of 3-(methyl alkoxy phosphoryl) propionic acid ester compound
  • Preparation method of 3-(methyl alkoxy phosphoryl) propionic acid ester compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Under nitrogen protection, in a 500ml four-neck round-bottomed flask equipped with mechanical stirring, a thermometer and a constant pressure dropping funnel, add 204 grams (1.5mol) of diethyl methyl phosphite, and then add the constant pressure drop Add 110.6 grams (1.515mol) of 99% acrylic acid in the funnel; cool down to 5°C, start dropwise reaction, temperature control is at 10°C, dropwise addition is completed in 2 hours, then insulated and stirred for 4 hours, and the reaction ends to obtain 3- (Methylethoxyphosphoryl) ethyl propionate product 288.0 grams, content 96.5%, yield 96.0%.

[0016] Structure detection data ( 1 HNMR (600MHz, CDCl 3 ): 84.16 (q, 2, J=7.3Hz, COOCH 2 CH 3 ) 4.07 (q, 2, J=7.3Hz, POCH 2 CH 3 ), 2.65-2.58 (m, 2, PCH 2 CH 2 COO) 2.09-2.04 (m, 2, PCH 2 CH2COO), 1.49(d, 3, J=13.7Hz, PCH3), 1.33(t, 3, J=7.0Hz, COOCH2CH3), 1.27(t, 3, J=7.1Hz, POCH2CH3);

[0017] 13 CNMR (600MHz, CDCl 3 ): δ172.06, 60.84, 60.10, 26.94, 24.80, 16.50, 14.07...

Embodiment 2

[0019] Under nitrogen protection, in a 500ml four-neck round-bottomed flask equipped with mechanical stirring, a thermometer and a constant pressure dropping funnel, add 162 grams (1.5mol) of dimethyl methylphosphite, and then add the constant pressure drop Add 110.3 grams (1.515mol) of 99% acrylic acid in the funnel; cool down to 5°C, start dropwise reaction, temperature control is at 0°C, dropwise addition is completed in 3 hours, then insulated and stirred for 5 hours, and the reaction ends to obtain 3- (Methylmethoxyphosphoryl) methyl propionate product 250.4 grams, content is 96.3%, yield 95.7%.

[0020] Structure detection data ( 1 HNMR (600MHz, CDCl 3 ): δ3.81 (d, 3,, COOCH 3 ), 3.53 (m, 3, POCH 3 ), 2.63-2.57 (m, 2, PCH 2 CH 2 COO), 2.07-2.01 (m, 2, PCH 2 CH 2 COO), 1.49 (d, 3, J=13.7Hz, PCH 3 );

[0021] 13 CNMR (600MHz, CDCl 3 ): δ172.7, 58.80, 58.10, 26.2, 24.30, 14.7).

Embodiment 3

[0023] Under nitrogen protection, in a 500ml four-necked round-bottomed flask equipped with mechanical stirring, a thermometer and a constant pressure dropping funnel, add 162 grams (1.5mol) of methyl dimethyl phosphite and 1000ml of toluene, and then add Add 110.3 grams (1.515 mol) of 99% acrylic acid into the pressure drop funnel; cool down to 5°C, start the dropwise reaction, control the temperature at 0°C, and complete the dropwise addition in 2.5 hours, then keep warm and stir for 8 hours, and the reaction ends. 250.1 g of methyl 3-(methylmethoxyphosphoryl)propionate were obtained, with a content of 96.6% and a yield of 95.9%.

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Abstract

The invention provides a preparation method of 3-(methyl alkoxy phosphoryl) propionic acid ester compound (I). Methyl ferro phosphoric acid dialkyl ester (III) and acrylic acid (II) are taken as raw materials to react under anhydrous and anaerobic conditions at 0 DEG C to 30 DEG C; and the reaction process is shown as the formula, wherein, R1 in the formula is equal to R2 and is methyl or ethyl. The product yield of the method can reach 96% and the operation is simple with no generation of three wastes, thus being beneficial to industrial amplifying production.

Description

technical field [0001] The invention relates to a preparation method of a compound, that is, a preparation method of 3-(methylalkoxyphosphoryl) propionate compounds. Background technique [0002] 3-(Methylalkoxyphosphoryl)propionate (I) is an important pesticide intermediate, which can be used in the synthesis of L-glufosinate. J.Org.Chem.1991,56,1783-1788 reported a kind of preparation method of 3-(methylethoxyphosphoryl) ethyl propionate compound, with ethyl acrylate and methylethoxyphosphoric acid as Raw materials, using sodium ethylate as a catalyst, react to obtain ethyl 3-(methylethoxyphosphoryl) propionate. The synthetic route is as follows: [0003] [0004] The product (I') yield of this reaction is low, only 81.4%, and after the reaction is completed, the catalyst, by-products and products need to be separated, the operation is loaded down with trivial details, and the three wastes produced in the reaction process are more. Not conducive to industrialized pro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/32
Inventor 任杰范谦晏三军
Owner LIER CHEM CO LTD
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