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Preparation method for 2-hydroxy-3-methoxy-methyl benzoate

A technology of methyl methoxybenzoate and methoxybenzaldehyde, which is applied in the field of preparation of pharmaceutical intermediates, can solve problems such as long synthetic routes, achieve the effects of simplifying operations, reducing by-products, and increasing overall yield

Inactive Publication Date: 2013-03-13
NANCHANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The purpose of this invention is to provide a kind of chemical synthesis method of the synthetic 2-hydroxyl-3-methoxybenzoic acid methyl ester of improvement, to overcome deficiencies such as long synthetic route of prior art

Method used

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  • Preparation method for 2-hydroxy-3-methoxy-methyl benzoate

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] 1, 2-hydroxyl-3-methoxybenzaldehyde is reacted with methanol, vanadium pentoxide and hydrogen peroxide, the reaction of 2-hydroxyl-3-methoxybenzaldehyde with methanol, vanadium pentoxide, hydrogen peroxide The molar ratio is 1:50:0.3:1.2, the reaction temperature is 5°C, and the reaction time is 8 hours.

[0018] 2. After the above steps are completed, filter, distill the filtrate under reduced pressure and condense to recover methanol, extract with diethyl ether, distill under reduced pressure and recover diethyl ether to obtain a crude product.

[0019] 3. The crude product was subjected to silica gel column chromatography to obtain methyl 2-hydroxy-3-methoxybenzoate.

[0020] The methanol recovered by distillation in step 2 is used for the reaction of step 1, the diethyl ether recovered by distillation can be reused in step 2, and the filter residue after filtering in step 2 is collected and processed to avoid environmental pollution.

Embodiment 2

[0022] 1, 2-hydroxyl-3-methoxybenzaldehyde is reacted with methanol, vanadium pentoxide and hydrogen peroxide, the reaction of 2-hydroxyl-3-methoxybenzaldehyde with methanol, vanadium pentoxide, hydrogen peroxide The molar ratio is 1:200:0.5:1.6, the reaction temperature is 25° C., and the reaction time is 4 hours.

[0023] 2. After the above steps are completed, filter, distill the filtrate under reduced pressure and condense to recover methanol, extract with diethyl ether, distill under reduced pressure and recover diethyl ether to obtain a crude product.

[0024] 3. The crude product was subjected to silica gel column chromatography to obtain methyl 2-hydroxy-3-methoxybenzoate.

[0025] The methanol recovered by distillation in step 2 is used for the reaction of step 1, the diethyl ether recovered by distillation can be reused in step 2, and the filter residue after filtering in step 2 is collected and processed to avoid environmental pollution.

Embodiment 3

[0027] 1, 2-hydroxyl-3-methoxybenzaldehyde is reacted with methanol, vanadium pentoxide and hydrogen peroxide, the reaction of 2-hydroxyl-3-methoxybenzaldehyde with methanol, vanadium pentoxide, hydrogen peroxide The molar ratio is 1:500:0.7:2, the reaction temperature is 50° C., and the reaction time is 1 hour.

[0028] 2. After the above steps are completed, filter, distill the filtrate under reduced pressure and condense to recover methanol, extract with diethyl ether, distill under reduced pressure and recover diethyl ether to obtain a crude product.

[0029] 3. The crude product was subjected to silica gel column chromatography to obtain methyl 2-hydroxy-3-methoxybenzoate.

[0030] The methanol recovered by distillation in step 2 is used for the reaction of step 1, the diethyl ether recovered by distillation can be reused in step 2, and the filter residue after filtering in step 2 is collected and processed to avoid environmental pollution.

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Abstract

The invention relates to a preparation method for 2-hydroxy-3-methoxy-methyl benzoate, comprising the following steps of: firstly, making 2-hydroxy-3-methoxybenzaldehyde react with methyl alcohol, vanadium pentoxide and hydrogen peroxide in the molar ratio of 1:(50-500):(0.3-0.7):(1.2-2) for 1-12 hours at the temperature of 0-60 DEG C; then filtering; carrying out reduced pressure distillation on filter liquor and condensing and collecting the methyl alcohol; extracting with diethyl ether; carrying out reduced pressure distillation and recovering the diethyl ether; and carrying out chromatography with a silica gel layer chromatographic column. The invention shortens the process route of preparing the 2-hydroxy-3-methoxy-methyl benzoate by the 2- hydroxy-3-methoxybenzaldehyde, reduces byproducts, simplifies the operation and increases the overall yield.

Description

technical field [0001] The invention belongs to the field of chemistry and chemical engineering, and in particular relates to a method for preparing a pharmaceutical intermediate. Background technique [0002] 2-Hydroxy-3-methoxybenzoic acid methyl ester is an important organic synthetic pharmaceutical intermediate, widely used in pharmaceutical synthesis industry. The published patent document WO2002092548A1 describes the preparation of 2-hydroxy-3-methoxybenzoic acid by oxidation of 2-hydroxy-3-methoxybenzaldehyde, and the published patent document WO2008144982A1 describes the use of 2-hydroxy-3-methoxybenzoic acid Esterification of oxybenzoic acid with methanol to prepare methyl 2-hydroxy-3-methoxybenzoate. The synthetic routes of these methods are long, take 2-hydroxyl-3-methoxybenzaldehyde as raw material synthetic 2-hydroxyl-3-methoxybenzoic acid methyl ester to go through multi-step reaction, total yield is low, by product is many, Many production processes are unfa...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/92C07C67/44
Inventor 张小林张贞发
Owner NANCHANG UNIV
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