A kind of preparation method of 2-(2-methoxyethoxy) acetaldehyde acetal

A technology of methoxyethoxy and acetaldehyde acetal, which is applied in the field of preparation of 2-acetaldehyde acetal, can solve the problems of unfavorable large-scale industrialization, high risk of operation, and low product purity, and achieve easy Large-scale industrialization, easy purification, and the effect of reducing production costs

Active Publication Date: 2017-07-18
CHENGDU LIKAI CHIRAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0015] The purpose of the present invention is to: provide a new preparation method of 2-(2-methoxyethoxy) acetaldehyde acetal (I), avoid the deficiencies of the existing methods, and solve the problems of high risk and high cost of the above-mentioned operations. Higher, lower product purity, unfavorable for large-scale industrialization and other issues

Method used

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  • A kind of preparation method of 2-(2-methoxyethoxy) acetaldehyde acetal
  • A kind of preparation method of 2-(2-methoxyethoxy) acetaldehyde acetal
  • A kind of preparation method of 2-(2-methoxyethoxy) acetaldehyde acetal

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Embodiment 1

[0042] The preparation method of 2-(2-methoxyethoxy) acetaldehyde dimethyl acetal (I)

[0043]Add 91.2 g of ethylene glycol monomethyl ether into the reaction flask, and add 40 g of sodium hydroxide under stirring to obtain a mixture; Water drops evaporate again, stop heating, and lower the temperature to below 60°C; add 124.5 g of 2-chloroacetaldehyde dimethyl acetal, and then heat to 130°C for reflux condensation reaction for 8 hours until the solution no longer refluxes; after the reaction is completed, Cool to room temperature, filter, collect the filtrate, add 18.7g of sodium chloride, heat to 50-60°C and keep stirring for 7 hours, then distill under reduced pressure, vacuum degree -0.09 MPa, collect 110-116°C fractions to obtain 2- (2-Methoxyethoxy)acetaldehyde dimethyl acetal, 152.3 g, purity 98.5%, yield 92.8%.

Embodiment 2

[0045] The preparation method of 2-(2-methoxyethoxy) acetaldehyde diethyl acetal (I)

[0046] Add 228 g of ethylene glycol monomethyl ether into the reaction flask, add 40 g of sodium hydroxide under stirring to obtain a mixture, heat the mixture to 100-130 °C for dehydration by distillation under reduced pressure, vacuum degree -0.08 MPa; react until there are no more water drops Evaporate, stop heating, and lower the temperature to below 60°C; add 197.1 g of 2-bromoacetaldehyde diethyl acetal, then heat to 130°C and react for 6 hours, then cool to room temperature; filter, collect the filtrate, add 9.9 g of magnesium sulfate, Keep warm at 20-30°C and stir for 10 hours, then distill under reduced pressure, vacuum degree -0.10 MPa, collect fractions at 115-120°C to obtain 2-(2-methoxyethoxy)acetaldehyde diethyl acetal, 175.9 g , 98.2% purity, 91.6% yield.

Embodiment 3

[0048] The preparation method of 2-(2-methoxyethoxy) acetaldehyde dimethyl acetal (I)

[0049] Add 114 g of ethylene glycol monomethyl ether into the reaction flask, and add 40 g of sodium hydroxide under stirring to obtain a mixture; Water drops evaporate again, stop heating, and lower the temperature to below 60 °C; add 167 g of 2-bromoacetaldehyde dimethyl acetal, and then heat to 130 °C for reflux condensation reaction for 8 hours until the solution no longer refluxes; after the reaction is completed, Cool to room temperature, filter, collect the filtrate, add 16.7g of sodium sulfate, heat to 70-80°C and keep stirring for 2 hours, then distill under reduced pressure, vacuum degree -0.09 MPa, collect 110-116°C fractions to obtain 2-( 2-methoxyethoxy) acetaldehyde dimethyl acetal, 147.6 g, purity 98.5%, yield 90%.

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Abstract

The invention discloses a preparation method of 2-(2-methoxyethoxy)acetaldehyde diethyl acetal, and belongs to the technical file of drug synthesis. The preparation method comprises the following steps: taking ethylene glycol monomethyl ether (II) as the primary raw material and reaction solvent, mixing (II) with sodium hydroxide, carrying out vacuum distillation to remove the water so as to obtain a strong-basic intermediate 2-methoxyl sodium ethoxide (III), directly reacting (III) with halogenated acetaldehyde diethyl acetal (IV) through a one-pot method to obtain a coarse product, decomposing the impurities by inorganic salts, and finally carrying out vacuum distillation to obtain the final product (I). The provided method has the advantages of low production cost, stable product quality, mild reaction conditions, safe and reliable operation, high repeatability and yield, and easy massive industrialization.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to a preparation method of 2-(2-methoxyethoxy) acetaldehyde acetal. Background technique [0002] Dirithromycin is a macrolide antibiotic and a prodrug of erythromycin. Its antibacterial activity is similar to that of erythromycin, but it has better pharmacokinetic properties and is well absorbed orally. With high availability and long half-life, it is widely used clinically in the treatment of acute exacerbation of chronic bronchitis, acute bronchitis, community-acquired pneumonia, pharyngitis and tonsillitis, and simple skin and soft tissue infections. It is a good medicine for erythromycin. Oral alternatives. [0003] 2-(2-Methoxyethoxy) acetaldehyde acetal is the key intermediate of the synthetic drug dirithromycin, and its chemical structural formula is as shown in compound (I), usually the following two types: 2-(2 -Methoxyethoxy) acetaldehyde dimethyl acetal (Ia, R=M...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C43/315C07C41/48
CPCC07C41/26C07C41/48C07C43/315C07C43/13
Inventor 袁伟成龙超久王川郑宁川周鸣强雷三忠陈宇袁仕雪
Owner CHENGDU LIKAI CHIRAL TECH
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