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Preparation method of 3-hydroxy-4-methoxyphenylpropylaldehyde

A technology of methoxyphenylpropanal and methoxyphenylacrolein, which is applied in the field of organic chemical synthesis, can solve the problems of high price, limited production, and few sources of isovanillin, so as to improve yield and purity, reduce cost effect

Pending Publication Date: 2021-11-09
绵阳三香汇生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In view of the above-mentioned shortcoming of the prior art, the purpose of the present invention is to provide a kind of preparation method of 3-hydroxyl-4-methoxyphenylpropionaldehyde, is used to solve the problem that isovanillin source is less in the prior art, and the price is expensive. , a problem that limits the production of 3-hydroxy-4-methoxyphenylpropanal intermediates

Method used

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  • Preparation method of 3-hydroxy-4-methoxyphenylpropylaldehyde
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  • Preparation method of 3-hydroxy-4-methoxyphenylpropylaldehyde

Examples

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Embodiment 1

[0049] A preparation method of 3-hydroxyl-4-methoxyphenylpropionaldehyde, comprising the steps of:

[0050] Step 1. Opening the loop: put 100g sassafras oil, 100g methanol, and 80g sodium hydroxide into the reaction kettle, heat up to 60°C after feeding and keep warm for reflux for 0.5h, then distill methanol out under normal pressure, and raise the temperature to 150°C , continue until the content of safrole in the reaction kettle is <1%, stop heating, wait for the reaction solution to cool to 80°C, slowly add 200g of distilled water, mix well, then pour the reaction solution into the separatory funnel, let stand to separate the phases, and separate the lower layer Aqueous phase, obtains potassium phenate solution;

[0051] Step 2. Etherification: Add the potassium phenate solution obtained in Step 1 into the reaction kettle, add excess dimethyl sulfate until the solution is clear and bright, and heat to 20°C for 9 hours, add excess toluene, mix well, and then stand for phase...

Embodiment 2

[0059] A preparation method of 3-hydroxyl-4-methoxyphenylpropionaldehyde, comprising the steps of:

[0060] Step 1. Opening the loop: Put 100g sassafras oil, 100g methanol, and 80g potassium hydroxide into the reaction kettle. After feeding, raise the temperature to 130°C for 5 hours. After the heat preservation and reflux, methanol is distilled out under normal pressure and the temperature is raised. To 160°C, continue until the content of safrole in the reactor <1%, stop heating, wait for the reaction solution to cool to 100°C, slowly add 230g distilled water, mix well, then pour the reaction solution into the separatory funnel, let stand to separate phases, Separating the lower floor water phase to obtain potassium phenate solution;

[0061] Step 2. Etherification: Add the potassium phenate solution obtained in Step 1 into the reaction kettle, add excess methyl trifluoromethanesulfonate until the solution is clear and bright, and heat to 100°C for 1 hour, add excess toluene...

Embodiment 3

[0069] A preparation method of 3-hydroxyl-4-methoxyphenylpropionaldehyde, comprising the steps of:

[0070] Step 1. Opening the loop: Put 100g sassafras oil, 100g methanol, and 80g sodium methoxide into the reaction kettle. After feeding, raise the temperature to 115°C for 3.5 hours. After the heat preservation and reflux, methanol is distilled out under normal pressure and the temperature is raised. To 155°C, continue until the content of safrole in the reactor <1%, stop heating, wait for the reaction solution to cool to 90°C, slowly add 220g of distilled water, mix well, then pour the reaction solution into the separatory funnel, let it stand for phase separation, Separating the lower floor water phase to obtain potassium phenate solution;

[0071] Step 2. Etherification: Add the potassium phenate solution obtained in Step 1 into the reaction kettle, add excess methyl p-toluenesulfonate until the solution is clear and bright, and heat to 75°C for 6 hours, add excess toluene,...

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Abstract

The invention provides a preparation method of 3-hydroxy-4-methoxyphenylpropylaldehyde. The preparation method comprises the following steps: 1, ring opening: subjecting sassafras oil, methanol and an alkaline reagent to a reaction to obtain a phenol potassium salt solution; 2, etherification: subjecting the phenol potassium salt solution to reacting with an excessive methylation reagent to obtain mixed ether; 3, hydrolysis: subjecting the mixed ether to reacting with alcohol, water and a catalyst to obtain a hydrolyzed oil phase; 4, esterification: subjecting the hydrolyzed oil phase to reacting with acetic anhydride to obtain an acetyl intermediate product; 5, ozonization and reduction: subjecting the acetyl product to reacting with ozone, and adding a pyrosulfite solution for reduction to obtain a reduced oil phase; 6, alcoholysis: performing alcoholysis on the oil phase obtained in the step 5 to obtain a crude isovanillin product; 7, condensation; and 8, hydrogenation. The preparation method solves the problems that isovanillin is few in source and high in price, and production of a 3-hydroxy-4-methoxyphenylpropyl aldehyde intermediate is limited in the prior art, and has the advantages of being high in yield and low in cost.

Description

technical field [0001] The invention relates to the field of organic chemical synthesis, in particular to a preparation method of 3-hydroxy-4-methoxyphenylpropanal. Background technique [0002] 3-Hydroxy-4-methoxyphenylpropanal is a new sweetener Advantame (N-{N-[3-(3-hydroxy-4-methoxyphenyl)propyl]-L-a- Aspartyl}-L-phenylalanine-1-methyl ester), an important synthetic intermediate, Advantame is a new type of high-power sweetener, with a sweetness up to 20,000 times that of sucrose, Advantame It has high safety, good stability and water solubility, and can be widely used in various foods. [0003] The preparation of 3-hydroxyl-4-methoxyphenylpropanal in the prior art generally takes isovanillin as a starting material, and 3-hydroxyl-4-methoxyphenylpropanal is obtained by aldol condensation with acetaldehyde and hydrogenation . [0004] However, isovanillin has few sources and is expensive, which limits the production of 3-hydroxy-4-methoxyphenylpropanal intermediates. ...

Claims

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Application Information

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IPC IPC(8): C07C45/40C07C47/58C07C45/74C07C45/69C07C47/277C07C37/00C07C37/66C07C39/235C07C39/08C07C41/16C07C43/23C07C67/08C07C69/157
CPCC07C45/40C07C47/58C07C45/74C07C45/69C07C37/00C07C37/66C07C41/16C07C67/08C07C47/277C07C39/235C07C43/23C07C69/157Y02P20/52
Inventor 张焜朱强熊智周锦
Owner 绵阳三香汇生物科技有限公司
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