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Method for preparing anisic aldehyde

A technology of p-methoxybenzaldehyde and p-hydroxybenzaldehyde, which is applied in the field of preparation of p-methoxybenzaldehyde, can solve the problems of low yield and unsuitability for large-scale industrial production, and achieve the effect of improving conversion rate

Active Publication Date: 2015-05-20
BEIJING RISUN TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] An object of the present invention is to provide a kind of p-methoxybenzaldehyde which is green, environment-friendly, high in yield and high in economic benefit for the problem that the synthetic method of p-methoxybenzaldehyde has low yield and is not suitable for large-scale industrial production in the prior art. The preparation method of oxybenzaldehyde

Method used

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  • Method for preparing anisic aldehyde
  • Method for preparing anisic aldehyde
  • Method for preparing anisic aldehyde

Examples

Experimental program
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Effect test

Embodiment 1

[0039] Take 0.05mol of p-hydroxybenzaldehyde and place it in a 250ml four-necked flask with a stirrer and a reflux device, add 20g of DMF, 0.005mol of tetramethylammonium chloride, and 0.0375mol of potassium carbonate; Add 0.124mol dimethyl carbonate, after the dropwise addition, heat up to 120°C and reflux for 3h to complete the reaction. After the reaction is completed, filter the reaction solution to recover potassium carbonate, recover the solvent by atmospheric distillation, and collect the 500 Pa, 140-150 ° C fraction by vacuum distillation at the bottom of the bottle to obtain the product p-methoxybenzaldehyde. DMF and by-product methanol are separated by rectification, and the tetramethylammonium chloride that has not participated in the reaction at the bottom of the bottle is recovered by recrystallization using by-product methanol.

[0040]Through analysis and calculation, the reaction yield is 88%, and the product purity is 98.84%.

Embodiment 2

[0042] Take 0.1mol of p-hydroxybenzaldehyde and place it in a 250ml four-neck flask equipped with a stirrer and reflux device, add 40g of DMF, 0.01mol of tetramethylammonium chloride, and 0.075mol of potassium carbonate; Add 0.124mol dimethyl carbonate, after the dropwise addition, heat up to 150°C and reflux for 5h to complete the reaction. After the reaction is completed, filter the reaction solution to recover potassium carbonate, recover the solvent by atmospheric distillation, and collect the 500 Pa, 140-150 ° C fraction by vacuum distillation at the bottom of the bottle, which is the product p-methoxybenzaldehyde. DMF and by-product methanol are separated by rectification, and the tetramethylammonium chloride that has not participated in the reaction at the bottom of the bottle is recovered by recrystallization using by-product methanol.

[0043] Through analysis and calculation, the reaction yield is 84%, and the product purity is 99.32%.

Embodiment 3

[0045] Take 0.075mol of p-hydroxybenzaldehyde and place it in a 250ml four-necked flask with a stirrer and a reflux device, add 30g of DMF, 0.009375mol of tetramethylammonium chloride, and 0.056mol of potassium carbonate; Add 0.124mol dimethyl carbonate, after the dropwise addition, heat up to 130°C and reflux for 5h to complete the reaction. After the reaction is completed, filter the reaction solution to recover potassium carbonate, recover the solvent by atmospheric distillation, and collect the 500 Pa, 140-150 ° C fraction by vacuum distillation at the bottom of the bottle, which is the product p-methoxybenzaldehyde. DMF and by-product methanol are separated by rectification, and the tetramethylammonium chloride that has not participated in the reaction at the bottom of the bottle is recovered by recrystallization using by-product methanol.

[0046] Through analysis and calculation, the reaction yield is 93%, and the product purity is 97.46%.

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Abstract

The invention provides a method for preparing anisic aldehyde. The method comprises the following steps: dissolving p-hydroxy benzaldehyde in an organic solvent, under the action of a catalyst composition, implementing methylation reaction with dimethyl carbonate, filtering and distilling the obtained reaction liquid, thereby obtaining anisic aldehyde, wherein the catalyst composition comprises a first catalyst as a phase transfer catalyst and a second catalyst selected from an alkaline catalyst, an acid catalyst or a biological enzyme catalyst; the mole ratio of p-hydroxy benzaldehyde, dimethyl carbonate and the first catalyst to the second catalyst is (0.5-1):1.24:(0.05-0.1):(0.2-0.75); the phase transfer catalyst is tetramethylammonium chloride, tetramethyl ammonium bromide or tetrabutylammonium bromide. The yield of a final target product of the method is greater than 90%, the product purity is greater than 99%, the utilization rate of dimethyl carbonate is 61%, and the process is safe, economic and environment-friendly.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a preparation method of p-methoxybenzaldehyde. Background technique [0002] p-Methoxybenzaldehyde, also known as anisaldehyde, is a colorless or light yellow liquid with a long-lasting aroma of hawthorn flowers. It is an important synthetic fragrance and can also be used in medicine, pesticide intermediates, and porphyrin photosensitizers intermediates, occupy a very important position in the food industry and daily chemical industry. The traditional synthesis method of anisaldehyde is prepared by the natural anisehole oxidation method, such as the oxidation of manganese dioxide reported in patent CN102336639A. The price of raw materials is high, the quantity is small, the planting is difficult, and the by-products are serious, and the discharge of three wastes is large. It is rarely used now. ;Patent CN103497094A obtained raw material anethole by isomerization of wormwood, an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/64C07C47/575
CPCC07C45/64C07C47/575
Inventor 张英伟苏思正张敏生曹亚林
Owner BEIJING RISUN TECH CO LTD
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