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Preparation method of methyl 5-formyl-2-methoxybenzoate

A technology of methyl methoxybenzoate and methyl methoxybenzoate, applied in the field of medicine, can solve problems such as low yield of methyl 5-formyl-2-methoxybenzoate, and achieve easy operation and control, short reaction steps and mild reaction conditions

Active Publication Date: 2018-12-28
山东轩硕医药科技有限公司
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Problems solved by technology

[0004] The invention provides a kind of preparation method of 5-formyl-2-methoxybenzoic acid methyl ester, to solve the problem of low yield of 5-formyl-2-methoxybenzoic acid methyl ester

Method used

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  • Preparation method of methyl 5-formyl-2-methoxybenzoate
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  • Preparation method of methyl 5-formyl-2-methoxybenzoate

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preparation example Construction

[0034] (1) the preparation of 2-methoxymethyl benzoate, reaction formula is as follows:

[0035]

[0036] (2) the preparation of 5-formyl-2-methoxybenzoic acid methyl ester, reaction formula is as follows:

[0037]

Embodiment 1

[0039] (1) Preparation of methyl 2-methoxybenzoate: add 150kg salicylic acid, 500L acetone, 225kg potassium carbonate to the reaction flask, heat up to 50-60°C, add 274kg dimethyl sulfate dropwise, and react for 3 hours , added 150kg potassium carbonate, 137kg dimethyl sulfate, reacted for 24 hours, after the reaction was completed, 300L of solvent was evaporated, cooled to 20°C, 500L of water was added, filtered, the filtrate was extracted with 500LDCM, and concentrated to obtain the product, 178.6kg, yield : 99%

[0040] (2) Preparation of methyl 5-formyl-2-methoxybenzoate: cool methyl 2-methoxybenzoate (100kg) and methanesulfonic acid (300L) to 0-10°C, add Hexatropine (252kg), heat up to 90°C, react for 16 hours, after the reaction is complete, cool down to room temperature, add 500L water into the reaction bottle, adjust ph=6-7 with sodium hydroxide solution, filter, and rinse the filter cake with water Wash and dry to obtain product, 109.8kg, yield 94%.

[0041] 1H NMR:...

Embodiment 2

[0043] (1) Preparation of methyl 2-methoxybenzoate: add 150kg salicylic acid, 500L acetone, 375kg potassium carbonate to the reaction flask, heat up to 50-60°C, slowly add 410kg dimethyl sulfate dropwise for 24 hours After dripping, keep stirring and react for 24 hours. After the reaction is completed, evaporate the solvent, cool down to 20°C, add 550L of water, filter, extract the filtrate with 500L of DCM, and concentrate to obtain the product, 175.3kg, yield: 97%

[0044] (2) Preparation of methyl 5-formyl-2-methoxybenzoate: cool methyl 2-methoxybenzoate (100kg) and methanesulfonic acid (400L) to 0-10°C, add Hexatropine (252kg), heat up to 80°C, react for 16 hours, after the reaction is complete, cool down to room temperature, add 500L water into the reaction bottle, adjust ph=6~7 with sodium hydroxide solution, filter, and rinse the filter cake with water Wash and dry to obtain the product, 99.3kg, yield 85.1%.

[0045] 1H NMR: (DMSO-d6,300MHz)6 9.92(5,1H),8.20-8.21(d,1H)...

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Abstract

The invention discloses a preparation method of methyl 5-formyl-2-methoxybenzoate. The preparation method comprises following steps: (1), preparation of methyl-2-methoxybenzoate; (2), preparation of methyl 5-formyl-2-methoxybenzoate. With the adoption of the method for loading an aldehyde group by urotropine after ester formation, the total yield can be increased to about 90%, the utilization rateof the raw materials is greatly increased, the cost is low, the operation is simple and convenient, and industrialization is facilitated.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a preparation method of methyl 5-formyl-2-methoxybenzoate. Background technique [0002] The new type is approved by the US FDA for the treatment of irritable bowel syndrome with diarrhea (IBS-D). Viberzi, which contains a new active ingredient, is administered orally with food twice a day. Viberzi activates receptors in the nervous system that reduce intestinal contractions. Viberzi aims to treat IBS-D in adults [0003] A kind of 5-formyl-2-methoxybenzoic acid methyl ester is the key intermediate of preparation, in the current prior art, such as WO2014 / 202580,2014, A1 introduced Viberzi (eluxadoline) about 5-formyl - The preparation method of methyl 2-methoxybenzoate adopts the method of adding aldehyde group first and then forming ester. The yield of the first step is only 16%, and the yield of the two steps is less than 10%, which is extremely low. Contents of the inven...

Claims

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Application Information

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IPC IPC(8): C07C67/343C07C69/92
CPCC07C67/11C07C67/343C07C69/92
Inventor 韩哲董岩岩孙亮
Owner 山东轩硕医药科技有限公司
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