Novel green method for preparing 2-diarylmethyl substituted-1-naphthol compound

Abstract

The invention provides a method for efficiently and highly selectively synthesizing 2-diarylmethyl substituted-1-naphthol compounds containing different substituted functional groups, which adopts phosphoric acid as a catalyst, adopts 1-naphthol compounds and 4-arylmethylene-2, 6-dialkyl-2, 5-cyclohexadiene-1-ketone compounds as reaction substrates, and adopts a one-pot method to synthesize the 2-diarylmethyl substituted-1-naphthol compounds containing different substituted functional groups. The reaction system takes water as a solvent. The method has the advantages that the catalyst is cheap and easily available; the substrate applicability is high; reaction conditions are mild, safe and reliable; the selectivity of the obtained target product is close to 100%, and the yield is high. The method overcomes the defects of poor reaction selectivity, tedious reaction steps, low yield, need of reagents harmful to the environment and the like in traditional synthesis of the 2-diarylmethyl substituted-1-naphthol compound, and has a good industrial application prospect. The invention also provides the corresponding 2-diarylmethyl substituted-1-naphthol compounds containing different substituted functional groups at the same time.

Description

technical field [0001] The present invention relates to the field of application catalytic synthesis of 2-diarylmethyl substituted-1-naphthol compounds, in particular to a method of combining 1-naphthol compounds with 4-aryl methylene-2,6- A new method for the efficient reaction of dialkyl-2,5-cyclohexadien-1-ones to prepare 2-diarylmethyl-substituted-1-naphthols. Background technique [0002] 2-Diarylmethyl-substituted-1-naphthol compounds and their derivatives are an important class of organic compounds, which are widely used in pharmaceutical intermediates, pesticide synthesis, biological probes, photovoltaic cells, polymer materials and asymmetric catalysis, etc. has wide application. [0003] The methods of synthesizing 2-alkyl / aryl substituted-1-naphthol compounds that have been reported in the literature mainly include: (1) Friedel-Crafts alkylation reaction: generally use strong Lewis acid (TiCl 4、 AlCl 3 , FeCl 3 , ZnBr 2 ) or strong Bronsted acids (HF or CF 3...

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Problems solved by technology

[0003] The methods of synthesizing 2-alkyl / aryl substituted-1-naphthol compounds that have been reported in the literature mainly include: (1) Friedel-Crafts alkylation reaction: generally use strong Lewis acid (TiCl 4、 AlCl 3 , FeCl 3 , ZnBr 2 ) or strong Bronsted acids (HF or CF 3 SO 3 H, etc.) Catalyze the alkylation reaction of alkyl halides and 1-naphthol, but strong acids are more serious to environmental pollution, and most strong acids are dangerous chemicals, which are more corrosive to equipment, and are used in industrial production processes. There is a big security risk in using

(2) Transition metals (Rh, Ir, Re, etc.) undergo oxidative addition reactions with the double bonds of olefins, and then undergo (oxidative) cross-coupling reactions or addition reactions with the 2-position C-H bonds of 1-naphthol, Thus the corresponding 2-alkyl / aryl substituted-1-naphthol compounds are obtained; however, the selectivity in the reaction process is poor, and there is a need to use special ligands (carbene or organic phosphine, etc.), and the catalyst preparation process is cumbersome , the catalyst is expensive and difficult to recycle, the reaction conditions are harsh, the product is low, and the functional group compatibility is poor.

[0004] So far, there is no report on the efficient synthesis of 2-diarylmethyl substituted-1-naphthols, and the reported 2-alkyl / aryl substituted-1-naphthols synthesis methods exist The quality of raw materials, the safety of production (Lewis acid is highly corrosive), the stability and purity of products, and other aspects are difficult, and the synthesis technology is relatively difficult. Currently, only a few companies in the United States, Japan and other countries are producing , while some products of 1-naphthol compounds in my country mainly rely on imports