A kind of preparation method of 8-methoxy-3,4-dihydro-1h-2-naphthalenone

Abstract

The invention relates to a method for preparing 8-methoxy-3,4-dihydro-1H-2-naphthalenone. The invention uses 2-methoxybenzonitrile as a starting material, and undergoes hydrolysis, reduction and other reactions. Synthesis of 8‑methoxy‑3,4‑dihydro‑1H‑2‑naphthalenone. It has the following advantages: 1) 2-methoxybenzonitrile benzonitrile raw material is cheap and easy to obtain, 2) the process reaction conditions are mild, the reaction time is short, the yield is high, the operation is simple, and it is easy to realize industrial production, 3) the process avoids Using expensive catalysts such as rhodium, etc., the production cost is lower. 4) The new magnetic nanoparticles used to load Lewis acid have good paramagnetic properties. For separation and recovery, they can be quickly separated and recycled from the reaction system using a simple external magnetic field. The process is simple, there is less waste, and the production cost is relatively low.

Description

technical field [0001] The invention relates to a method for preparing 8-methoxy-3,4-dihydro-1H-2-naphthone, specifically a method for preparing 8-methoxybenzonitrile with 2-methoxybenzonitrile as raw material The method of base-3,4-dihydro-1H-2-naphthalenone. [0002] The invention uses 2-methoxybenzonitrile as a starting material to synthesize 8-methoxy-3,4-dihydro-1H-2-naphthalene through reactions such as hydrolysis and reduction. Background technique [0003] 8-methoxy-2-naphthalenone is an important starting material for the synthesis of dopamine receptor agonists and serotonin receptor inhibitors. [0004] The existing preparation method of 8-methoxy-2-naphthyl ketone is: at first is to synthesize 2-methoxyphenylacetic acid, then 2-methoxyphenylacetic acid is cyclized under catalyst catalysis to obtain 8-methoxy-3 ,4-Dihydro-1H-2-naphthone. [0005] The relevant literature reports about 2-methoxyphenylacetic acid mainly include: [0006] In 1948, Levine, Joseph et...

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Problems solved by technology

[0010] In 2011, Liu, Zhi-Qiang et al. (Liu, Zhi-Qiang et al. Gene Cloning, Expression, and Characterization of a Nitrilase from Alcaligenes faecalis ZJUTB10. Journal of Agricultural and Food Chemistry, 59(21), 11560-11570; 2011) reported Using 2-methoxyphenylacetonitrile as raw material to synthesize 2-methoxyphenylacetic acid, the method used is biological enzyme enzymatic method (nitrilase). Although this method is environmentally friendly, its nitrilase is difficult to extract from microorganisms. extract

[0011] In 2012, Yao Yi et al. (Yao Yi et al. Research on the synthesis process of methoxyphenamine hydrochloride. Chemical Production and Technology, 19(1), 7-9; 2012) reported the use of o-hydroxyphenylacetic acid as raw material and dimethyl sulfate The reaction produces 2-methoxyphenylacetic acid with a yield of about 92%, but the dimethyl sulfate used is more toxic

[0021] In 2004, Claudio C.Silveira et al. (Claudio C.Silveira et al.Synthetic approaches to 2-tetralones.Tetrahedron, 2004,60:8295–8328) reviewed the synthetic method of 2-naphthylone derivatives, for 8-methoxy- The synthesis of 2-naphthone is through the Buchner reaction under the condition of rhodium catalyst, and then in the presence of trifluoroacetic acid, the target product is generated, wherein the rhodium catalyst is more expensive

[0023] The preparation process of 8-methoxy-3,4-dihydro-1H-2-naphthone disclosed in the above-mentioned patents has many deficiencies, such as many side reactions, expensive catalysts, long reaction time, high production cost, post-treatment Problems such as large amount of waste water, corrosiveness to equipment and serious environmental pollution

[0024] The present invention takes 2-methoxybenzonitrile as the starting material, and the method for preparing 8-methoxy-3,4-dihydro-1H-2-naphthone through reactions such as hydrolysis, reduction, halogenation, and substitution has not yet been See related literature and patent reports

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