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A kind of preparation method of o-methoxybenzaldehyde

A technology of o-methoxybenzaldehyde and methoxybenzaldehyde is applied in the field of preparation of o-methoxybenzaldehyde, and can solve the problems of complex synthesis method of o-methoxybenzaldehyde, low product yield and purity, and reaction conditions. Harsh and other problems, to achieve the effect of reducing reaction temperature and solvent consumption, high yield and purity, and simple preparation process

Active Publication Date: 2020-08-04
WUHAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In view of this, the present invention aims to propose a kind of preparation method of o-methoxybenzaldehyde, to solve existing o-methoxybenzaldehyde synthetic method complexity, long reaction time, harsh reaction conditions, product yield and purity are lower , Environmental pressure problems

Method used

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  • A kind of preparation method of o-methoxybenzaldehyde
  • A kind of preparation method of o-methoxybenzaldehyde
  • A kind of preparation method of o-methoxybenzaldehyde

Examples

Experimental program
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Embodiment 1

[0037] A preparation method for o-methoxybenzaldehyde, specifically comprising the following steps:

[0038] 1) 12.0mg (0.1mmol) of o-tolualdehyde, 64.0mg (20.0mmol) of anhydrous methanol (MeOH), 2.25mg (0.01mmol) of palladium acetate (Pd(OAc) 2 ), 54.0mg (0.2mmol) potassium persulfate (K 2 S 2 o 8 ), 6.44mg (0.04mmol) of m-trifluoromethylaniline (TDG) were mixed in 1ml of dichloromethane (DCM), and then stirred and reacted on a magnetic stirrer at 60°C for 24h, that is, in o-tolualdehyde The methoxylation reaction of the ortho position of the aldehyde group obtains the reaction solution A. During the reaction, the specification can be -254 thin-layer chromatographic plate spot plate to track whether the reaction is complete;

[0039] 2) filter the reaction solution A, and add saturated sodium bicarbonate aqueous solution and dichloromethane to the filtered filtrate B for extraction to obtain the lower layer extract C, wherein the volume ratio of saturated sodium bicarbon...

Embodiment 2

[0056] The difference between this embodiment and Example 1 is that in this embodiment, the aniline ligand that condenses with the aldehyde group in o-tolualdehyde to form a transient directing group is o-trifluoromethylaniline, and the amount of o-trifluoromethylaniline Be 6.44mg (0.04mmol), other preparation raw material composition and the preparation process of o-methoxybenzaldehyde are the same as embodiment 1.

[0057] The amount of o-methoxybenzaldehyde obtained in this embodiment is 6.75 mg, and the calculated yield is 45%.

Embodiment 3

[0059] The difference between this embodiment and Example 1 is: in this embodiment, the oxidant is sodium persulfate, and its consumption is 47.6 mg (0.2 mmol), and the composition of other preparation raw materials and the preparation process of o-methoxybenzaldehyde are the same as in Example 1.

[0060] The amount of o-methoxybenzaldehyde obtained in this example was 7.35 mg, and the calculated yield was 49%.

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Abstract

The invention provides an o-methoxybenzaldehyde preparation method, which comprises: 1) mixing a benzaldehyde-based derivative, anhydrous methanol, palladium acetate, an oxidizing agent and an aniline ligand in a solvent, and carrying out a methoxylation reaction under a certain temperature condition to obtain a reaction liquid A; 2) filtering the reaction liquid A, and extracting the obtained filtrate B with an extractant to obtain a lower layer extracting liquid C; 3) drying the extracting liquid C with a drying agent to remove water, filtering, adding silica gel powder to the obtained filtrate D, and carrying out rotary evaporation to remove dichloromethane to obtain a mixture E; and 4) separating and purifying the mixture E through chromatography to obtain o-methoxybenzaldehyde. According to the present invention, the prepared o-methoxybenzaldehyde has high yield and high purity, wherein the yield can reach 67%; and the method has characteristics of simple preparation process, easy operation, short reaction time and substantially increased production efficiency.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of o-methoxybenzaldehyde. Background technique [0002] O-methoxybenzaldehyde is a common intermediate in organic synthesis, which widely exists in drugs and natural products, such as the adrenaline-mimetic drug Chuankening. It can also be used as an intermediate in spices, pharmaceuticals and fluorescent whitening agents, such as the production of fluorescent whitening agent CBS, triphenylmethane dyes and mothproof agent N. [0003] Due to the weak coordination of the aldehyde group and the sensitivity to the oxidant and the weak guiding effect, it is difficult to position the benzaldehyde in the ortho position. Secondly, the hydroxyl H in the methanol is not easy to leave, making it difficult to position the methoxy group in the reaction. The aldehyde group is in the ortho position, and many existing synthesis methods of o-methoxybenzaldehyde hav...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/64C07C45/80C07C45/79C07C47/575
CPCC07C45/64C07C45/79C07C45/80C07C47/575
Inventor 张雪琼董雯丹李峰张方林
Owner WUHAN UNIV OF TECH
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