Preparation method of o-anisaldehyde

Abstract

The invention discloses a preparation method of o-anisaldehyde. The preparation method comprises the following steps of adding toluene, salicylaldehyde and n-butylamine into a container, carrying out stirring and oil bath heating reflux in an argon protective atmosphere for 5h, carrying out cooling, removing a solvent, carrying out ethanol recrystallization to obtain a salicylaldehyde-succimide condensation product, adding DMSO, the salicylaldehyde-succimide condensation product, dimethyl carbonate and KOH into the container, carrying out heating in an argon protective atmosphere to a temperature of 85 DEG C with stirring, carrying out a thermostatic reaction process for 24h, cooling the reaction liquid to a room temperature, filtering to remove KOH, adding HCl and ethyl acetate into the filtrate, carrying out full vibration, separating an organic layer, extracting a water layer by ethyl acetate, merging organic phases, washing the organic phases by a saturated common salt solution, carrying out drying, and carrying out evaporation to remove the organic solvent. The preparation method utilizes a mixed solvent of ethyl acetate and petroleum ether as an eluant and can produce colorless o-anisaldehyde crystals by column chromatography and change of solvent polarity gradient. The preparation method has the advantages of simple processes, mild conditions, good controllability, operation safety, industrial production easiness, high yield and low production cost.

Description

technical field [0001] The invention relates to a preparation method of o-anisaldehyde. Background technique [0002] O-anisaldehyde (also known as 2-methoxybenzaldehyde, o-methoxybenzaldehyde or salicylaldehyde methyl ether) is an important organic synthesis intermediate, mainly used in dyes, fragrances, medicines and fluorescent whitening agents production. For example, o-anisaldehyde can be used in the production of adrenaline-mimetic drug Chuankening, triphenylmethane dyes and moth-proofing agents. [0003] According to Document 1 [Zhang Sigui. Handbook of Practical Fine Chemicals. Beijing: Chemical Industry Press, 1996.1655], Document 2 [Gao Hongbin, Dictionary of Practical Organic Chemistry. Beijing: Higher Education Press, 1997.745] and Document 3 [Qiao Qingdong, Zhao Huixin , Pu Xueyong. The synthesis of m-tetra-methoxyphenylporphyrin. Fine Chemical Industry, 1999.16 (1): 31], the reported o-anisaldehyde synthesis method is as follows: [0004] (1) [0005] ...

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Problems solved by technology

[0006] It can be seen from the above: method (1) has many steps, the conditions are not easy to control, and the post-treatment is also cumbersome and time-consuming; method (2) uses a strong oxidant such as potassium permanganate to oxidize the arylmethyl group to the aldehyde group, and the latter may be destroyed. Further oxidation into carboxyl groups, if the reaction stays in the aldehyde stage, the control and operation of the reaction conditions are more difficult; method (3) has the characteristics of safe operation, convenience, mild conditions and easy industrial production, but the yield of the product is only about 60%

Moreover, methods (1) and (3) both use toxic dimethyl sulfate, which brings certain inconvenience and danger to actual production

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