Method for preparing 4-acetyl-1-naphthoic acid

By using 1-bromonaphthalene as the starting material and using a multi-step reaction under mild conditions to synthesize 4-acetyl-1-naphthoic acid, the problems of expensive raw materials and harsh reaction conditions in the existing technology have been solved, and high efficiency and low cost have been achieved. The intermediate synthesis is suitable for industrial production.

CN115448831AActive Publication Date: 2022-12-09北京元延医药科技股份有限公司
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Patent Information

Application Number
CN202211407449.0
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2022-11-10
Publication Date
2022-12-09
Estimated Expiration
2042-11-10

AI Technical Summary

Technical Problem

The existing method for synthesizing 4-acetyl-1-naphthoic acid, an important intermediate of aforana, has the problems of expensive raw materials, harsh reaction conditions, low yield and unsuitable for industrial production, especially commercially available 4-bromo Naphthylethanone is expensive, uses highly toxic potassium cyanide and reacts at high temperatures, and some methods require an aqueous environment or precious metal catalysts, resulting in higher costs.

Method used

1-Bronaphthalene is used as the starting material to synthesize 4-acetyl-1-naphthoic acid through a multi-step reaction, including the use of reactants such as methanol, trimethyl formate, toluenesulfonic acid, tetrahydrofuran, n-butyllithium and carbon dioxide. , controlling the reaction conditions to be mild, using methyl tert-butyl ether for extraction, avoiding highly toxic substances and high-temperature reactions, and reducing raw material costs.

Benefits of technology

The efficient synthesis of 4-acetyl-1-naphthoic acid is achieved, the raw materials are easily available, the reaction conditions are mild, and it is suitable for industrial production. It avoids the use of high costs and dangerous reagents, and improves the yield and product purity.

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Abstract

The invention relates to a method for preparing 4-acetyl-1-naphthoic acid. Specifically, the method for preparing the 4-acetyl-1-naphthoic acid comprises the following steps: in an organic solvent (such as methanol, ethanol, acetone, acetonitrile and the like), in the presence of a catalyst (such as p-toluenesulfonic acid, benzenesulfonic acid, p-ethylbenzene sulfonic acid and the like), reacting 4-bromo-1-naphthyl ethyl ketone with trimethyl orthoformate to obtain 4-bromo-1-(1, 1-dimethoxyethyl) naphthalene; the method comprises the following steps: reacting 4-bromo-1-(1, 1-dimethoxyethyl) naphthalene with n-butyllithium in an organic solvent (such as tetrahydrofuran, dichloromethane, dichloroethane and the like), then adding carbon dioxide to react, and then adding an acid (such as inorganic acid, such as hydrochloric acid, sulfuric acid, nitric acid and the like) to react to obtain 4-acetyl-1-naphthoic acid. The method provided by the invention has one or more excellent effects, for example, the reaction conditions are mild, and industrial-specification production is easy to realize.
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