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Preparation method of (E)-2-[2-(6-pyrimidine-4-yloxy) phenyl]-3-methoxyacrylate

A technology of methyl methoxyacrylate and methyl dimethoxypropionate, applied in the field of preparation of methyl-2-[2-phenyl]-3-methoxyacrylate, can solve the problem of low reaction yield , Catalytic efficiency is not high, affect the yield of methyl acrylate and other problems, to achieve the effect of increasing product yield, catalytic efficiency and conversion rate

Active Publication Date: 2011-02-16
CHONGQING UNISPLENDOUR CHEM
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Problems solved by technology

[0007] In the above method, directly adding the base into the reaction system as a catalyst still has the problems of low catalytic efficiency and low reaction yield, which in turn affects the performance of (E)-2-[2-(6-chloropyrimidin-4-yl) Oxygen) phenyl] - the productive rate of methyl 3-methoxyacrylate

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  • Preparation method of (E)-2-[2-(6-pyrimidine-4-yloxy) phenyl]-3-methoxyacrylate
  • Preparation method of (E)-2-[2-(6-pyrimidine-4-yloxy) phenyl]-3-methoxyacrylate
  • Preparation method of (E)-2-[2-(6-pyrimidine-4-yloxy) phenyl]-3-methoxyacrylate

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preparation example Construction

[0026] The embodiment of the present invention discloses a preparation method of (E)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxymethyl acrylate, comprising:

[0027] a. Calcining and grinding the basic catalyst successively and then heating and activating to obtain an activated catalyst;

[0028] b, 3,3-dimethoxy-2-(2-hydroxyphenyl)propionic acid methyl ester and 4,6-dichloropyrimidine are subjected to a substitution reaction in the presence of the activated catalyst to obtain 2- Methyl [2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionate;

[0029] c, the prepared 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester is subjected to dealcoholization reaction to obtain (E)-2- Methyl [2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxyacrylate.

[0030] Step a is a process of activating the catalyst. The activation process specifically includes calcining and grinding the basic catalyst and then heating and activating it. Since the substitu...

Embodiment 1

[0046] 1. Put K 2 CO 3 Put it into a muffle furnace and calcinate at 360°C for 3.5h, then grind it to 120 mesh, and grind the K 2 CO 3 Keep at 30mmHg and 95°C for 3.5h to obtain an activated catalyst.

[0047] 2, add DMF, 1mol3 in reaction vessel, the activation catalyst that 3-dimethoxy-2-(2-hydroxyphenyl) methyl propionate, 2mol4, 6-dichloropyrimidine and 2mol step 1 make, will Heat the reaction vessel to 60°C, finish the reaction after 8 hours of reaction, filter the solution in the reaction vessel, distill the filtrate under reduced pressure to remove DMF, then dissolve the distilled mixture with ethyl acetate and filter, wash the filtrate with water, dry and filter , Atmospheric distillation, and vacuum distillation to obtain 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester.

[0048] 3. Add NaHSO to methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionate prepared in step 1 4 , reacted at 160°C for 2 hours under 20mmHg, d...

Embodiment 2

[0051] 1. Na 2 CO 3 Put it into a muffle furnace and calcined at 320°C for 3.5h, then grind to 100 mesh, and the ground Na 2 CO 3 Keep at 30mmHg and 80°C for 3.5h to obtain an activated catalyst.

[0052] 2. Add DMF (N,N dimethylformamide), 2mol 3,3-dimethoxy-2-(2-hydroxyphenyl)propionic acid methyl ester, 3.2mol 4,6-dichloropyrimidine to the reaction vessel and 3.2mol of the activated catalyst prepared in step 1, the reaction vessel was heated to 60°C, and the reaction was completed after 8 hours of reaction, the solution in the reaction vessel was filtered, the filtrate was distilled under reduced pressure to remove DMF, and then the distilled mixture was distilled with ethyl acetate After the ester is dissolved, it is filtered, and the filtrate is washed with water, dried, filtered, distilled at atmospheric pressure, and distilled under reduced pressure to obtain 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxy Methyl propionate.

[0053] 3. Add KHSO to methyl 2-[...

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Abstract

The invention provides a preparation method of (E)-2-[2-(6-pyrimidine-4-yloxy) phenyl]-3-methoxyacrylat, which comprises the steps of: sequentially calcining and grinding a basic catalyst and then heating for activating to obtain an activated catalyst; carrying out a substitution reaction on 3,3-dimethoxy-2-(2-hydroxyphenyl) methyl propionate and 4,6-dichloropyrimidine in the presence of the activated catalyst, and then carrying out a dealcohol reaction on the 2-[2-(6-pyrimidine-4-yloxy) phenyl]-3,3-dimethoxy methyl propionate obtained from the substitution reaction to obtain the (E)-2-[2-(6-pyrimidine-4-yloxy) phenyl]-3-methoxyacrylat. In the method, the basic catalyst is activated, which improves the catalysis efficiency of the catalyst and increases the conversion rate of the raw materials in the same reaction time, thus the product yield of the substitution reaction is improved, and the product yield of the dealcohol reaction is enhanced.

Description

technical field [0001] The invention relates to the field of fungicides, in particular to a method for preparing methyl (E)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxyacrylate. Background technique [0002] Azoxystrobin is a methyl methacrylate fungicide, which has good activity against most fungal diseases, such as powdery mildew, rust, glume blight, net spot, downy mildew, and rice blast. Azoxystrobin is widely used in foliar sprays and seed treatments, as well as soil treatments. Azoxystrobin is an environmentally friendly fungicide that is safe to crops, has no phytotoxicity, and will not pollute groundwater when used at the recommended dose. [0003] (E)-2-[2-(6-chloropyrimidin-4-yl oxygen) phenyl]-3-methyl methoxyacrylate is an important intermediate for the synthesis of azoxystrobin, and its structure is as shown in formula (I) Show. (E)-2-[2-(6-chloropyrimidin-4-yloxygen) phenyl]-3-methoxy methyl acrylate is usually first prepared with 3,3-dimethoxy-2- (2-H...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/34
CPCC07D239/34
Inventor 姚如杰金海琴周垂龙刘丹杨建川胡捷
Owner CHONGQING UNISPLENDOUR CHEM
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