CN112679321A - Green novel method for preparing 1-diarylmethyl substituted-2-naphthol compound - Google Patents

Green novel method for preparing 1-diarylmethyl substituted-2-naphthol compound Download PDF

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CN112679321A
CN112679321A CN202110129716.1A CN202110129716A CN112679321A CN 112679321 A CN112679321 A CN 112679321A CN 202110129716 A CN202110129716 A CN 202110129716A CN 112679321 A CN112679321 A CN 112679321A
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butyl
methylene
cyclohexadiene
cyclohexadien
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CN112679321B (en
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熊碧权
尚文丽
许卫凤
唐课文
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Hunan Institute of Science and Technology
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Abstract

The invention provides a method for efficiently and selectively synthesizing 1-diaryl methyl substituted-2-naphthol compounds containing different substituted functional groups, which adopts phosphoric acid as a catalyst, 2-naphthol compounds and 4-arylmethylene-2, 6-dialkyl-2, 5-cyclohexadiene-1-ketone compounds as reaction substrates, and water as a solvent in a reaction system. The method has the advantages that: the catalyst is cheap and easy to obtain; the substrate applicability is high; the reaction condition is mild, safe and reliable; the selectivity of the obtained target product is close to 100 percent, and the yield is up to more than 90 percent. The method overcomes the defects of poor reaction selectivity, complicated reaction steps, low yield, the need of using reagents harmful to the environment and the like in the traditional synthesis of the 1-diaryl methyl substituted-2-naphthol compound, and has good industrial application prospect. The invention also provides corresponding 1-diarylmethyl substituted-2-naphthol compounds containing different substituted functional groups.

Description

Green novel method for preparing 1-diarylmethyl substituted-2-naphthol compound
Technical Field
The invention relates to the field of application catalytic synthesis of 1-diarylmethyl substituted-2-naphthol compounds, in particular to a novel method for preparing 1-diarylmethyl substituted-2-naphthol compounds by efficiently reacting 2-naphthol compounds with 4-arylmethylene-2, 6-dialkyl-2, 5-cyclohexadiene-1-ketone compounds.
Background
1-diaryl methyl substituted-2-naphthol compounds and derivatives thereof are important organic compounds and have wide application in the aspects of medical intermediates, pesticide synthesis, polymerization materials, asymmetric catalysis and the like.
The method for synthesizing the 1-alkyl/aryl substituted-2-naphthol compound reported in the literature mainly comprises the following steps: (1) friedel-crafts alkylation reaction: with strong Lewis acids (TiCl) in general4、AlCl3、FeCl3、ZnBr2) Or strong Bronsted acids (HF or CF)3SO3H, etc.) to catalyze the alkylation reaction of alkyl halide and 2-naphthol, but strong acid has serious environmental pollution, most of the strong acid belongs to dangerous chemicals, has strong corrosivity to equipment, and has great potential safety hazard when used in the industrial production process. (2) The transition metal (Rh, Ir, Re, etc.) is subjected to oxidation addition reaction with double bonds of olefin, and further subjected to (oxidation) cross coupling reaction or addition reaction with 1-site C-H bonds of 2-naphthol to prepare the corresponding 1-alkyl/aryl substituted-2-naphthol compound; however, in the reaction process, special ligands (carbene or organic phosphine and the like) are required to be adopted, and the preparation process of the catalyst is complicated, the catalyst is expensive and difficult to recycle, the reaction conditions are harsh, the selectivity and the product are low, the functional group compatibility is poor, and the like.
So far, no efficient synthesis method of the 1-diaryl methyl substituted-2-naphthol compound is reported, the reported synthesis method of the 1-alkyl/aryl substituted-2-naphthol compound has the problems of raw material quality, production safety (Lewis acid has strong corrosivity), product stability and purity and the like, the synthesis technology is difficult, only a plurality of companies in the countries of America, Japan and the like are used for production at present, and partial products of the 2-naphthol compound in China mainly depend on import at present.
Aiming at the defects of the existing synthesis process of 2-naphthol compounds and derivatives thereof, the industry is focusing on developing a novel method for preparing corresponding 1-diarylmethyl substituted-2-naphthol compounds by using stable, cheap and easily available 2-naphthol compounds as synthesis building blocks through high-efficiency catalysis by using cheap catalysts.
Disclosure of Invention
The invention aims to provide a novel method for efficiently and selectively synthesizing a corresponding 1-diarylmethyl substituted-2-naphthol compound by using a cheap and easily-obtained 2-naphthol compound and a 4-arylmethylene-2, 6-dialkyl-2, 5-cyclohexadiene-1-one compound as raw materials so as to overcome the defects in the prior art.
The invention comprises the following steps: taking a reaction amount of 2-naphthol compound, 4-arylmethylene-2, 6-dialkyl-2, 5-cyclohexadiene-1-one, a catalyst and a solvent, placing the mixture in a reaction vessel under the condition of nitrogen, mixing the mixture under stirring at 25-120 DEG CoAnd reacting for 8-14 hours at the temperature of C to obtain the corresponding 1-diaryl methyl substituted-2-naphthol compound containing different substituted functional groups. The specific reaction formula is as follows:
Figure 123684DEST_PATH_IMAGE001
（I）
wherein,
the catalyst is selected from phosphoric acid (H)3PO4) The solvent is selected from water;
ar is selected from phenyl, 2-methylphenyl, 4-methylphenyl, 2-hydroxyphenyl, 4-ethylphenyl, 4-tert-butylphenyl, 4-isopropoxyphenyl, 4-benzyloxyphenyl, 3-methoxyphenyl, 2, 5-dimethoxyphenyl, 3-cyanophenyl, 4-trifluoromethylphenyl, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-bromophenyl group, 3-bromophenyl group, 4-bromophenyl group, 3-nitrophenyl group, 3-methoxy-4-hydroxyphenyl group, 4-aldehyde phenyl group, 2-pyridyl group, 6-benzo-2, 3-dihydrofuryl group, 2-thienyl group, 3-thienyl group;
R1is methyl, isopropyl, tert-butyl;
R2is 6-cyano, 6-bromo, 7-bromo, 6-methoxy, 3-hydroxy, 7-hydroxy, 6-carbomethoxy, 7-methoxy, 6-carboxy, 6-aldehyde group.
In the above method for synthesizing a 1-diarylmethyl-substituted-2-naphthol compound from a 2-naphthol compound and a 4-arylmethylene-2, 6-dialkyl-2, 5-cyclohexadiene-1-one compound, the 4-arylmethylene-2, 6-dialkyl-2, 5-cyclohexadiene-1-one is selected from 4-phenylmethylene-2, 6-di-t-butyl-2, 5-cyclohexadiene-1-one, 4- (2-methylphenyl) methylene-2, 6-di-t-butyl-2, 5-cyclohexadiene-1-one, 4- (4-methylphenyl) methylene-2, 6-di-t-butyl-2, 5-cyclohexadien-1-one, 4- (2-hydroxyphenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, 4- (4-ethylphenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, 4- (4-tert-butylphenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, 4- (4-isopropoxyphenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, 4- (4-benzyloxyphenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, 4- (3-methoxyphenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, 4- (2, 5-dimethoxyphenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, 4- (3-cyanophenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, 4- (4-trifluoromethylphenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, 4- (2-fluorophenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, 4- (3-fluorophenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, 4- (4-fluorophenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, 4- (2-bromophenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, 4- (3-bromophenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, 2-methyl-ethyl-methyl-1-one, 4- (4-bromophenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, 4- (3-nitrophenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, 4- (3-methoxy-4-hydroxyphenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, 4- (4-formylphenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, 4- (2-pyridyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, and mixtures thereof, 4- (6-benzo-2, 3-dihydrofuranyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, 4- (2-thienyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, 4- (3-thienyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, 4-phenylmethylene-2, 6-dimethyl-2, 5-cyclohexadien-1-one, 4-phenylmethylene-2, 6-diisopropyl-2, 5-cyclohexadien-1-one.
In the above method for synthesizing 1-diarylmethyl-substituted-2-naphthol from 2-naphthol and 4-arylmethylene-2, 6-dialkyl-2, 5-cyclohexadiene-1-one compound, the 2-naphthol is selected from 6-cyano-2-naphthol, 6-bromo-2-naphthol, 7-bromo-2-naphthol, 6-methoxy-2-naphthol, 2, 3-dihydroxynaphthalene, 2, 7-dihydroxynaphthalene, 6-hydroxy-2-naphthylmethyl ester, 7-methoxy-2-naphthol, 6-hydroxy-2-naphthoic acid.
In the method for synthesizing the 1-diarylmethyl-substituted-2-naphthol compound from the 2-naphthol compound and the 4-arylmethylene-2, 6-dialkyl-2, 5-cyclohexadiene-1-one compound, the molar ratio of the 4-arylmethylene-2, 6-dialkyl-2, 5-cyclohexadiene-1-one compound to the 2-naphthol compound is [1:1 ]; the mol ratio of the 4-arylmethylene-2, 6-dialkyl-2, 5-cyclohexadiene-1-ketone compound to the phosphoric acid is 1: [0.01-0.2].
The method for efficiently and selectively synthesizing the 1-diaryl methyl substituted-2-naphthol compound from the 2-naphthol compound and the 4-arylmethylene-2, 6-dialkyl-2, 5-cyclohexadiene-1-one compound has mild and easily controlled reaction process. The method is simple and easy to implement, green and environment-friendly while obtaining high yield and 100% selectivity, and the used catalyst is cheap and easy to obtain, is simple to prepare and has good industrial application prospect.
Detailed Description
The invention is further illustrated below with reference to examples of the invention:
first, testing and analyzing
Structural analysis, target product selectivity and yield of the reaction products in the following examples of the present invention gas chromatographs (6890N) equipped with HP-5MS capillary chromatography columns (30 m.times.0.45 mm.times.0.8 μm) manufactured by Agilent, gas-mass spectrometers GC/MS (6890N/5973N) and Bruker Avance-III 500 NMR analyzers manufactured by Bruker were used.
Second, example
Example 1
28.8 mg (0.2mmol) of 2-naphthol, 58.8 mg (0.2mmol) of 4-phenylmethylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, phosphoric acid (0.002 mmol, 0.01 mmol, 0.02 mmol, 0.04mmol) and 1.0mL of water were added under nitrogen to a Schlenk tube at 100 deg.FoC stirring the reaction for 8 hours. The yield of the reaction was most optimal when the amount of phosphoric acid used was 0.01 mmol as determined by gas chromatography yield assay, which was 97%.
Example 2
28.8 mg (0.2mmol) of 2-naphthol, 58.8 mg (0.2mmol) of 4-phenylmethylene-2, 6-di-tert-butyl-2, 5-cyclohexadiene-1-one, (0.01 mmol) of phosphoric acid and 1.0mL of water were charged under nitrogen into a Schlenk tube, and the mixture was placed in 25 mL of Schlenk tubeoC, 40 oC, 60 oC, 80 oC, 100 oC and 120oC the reaction was stirred for 14 hours. By gas chromatography yield detection and analysis, when the reaction temperature is 100 DEGoAt C, the results are optimal, with a yield of 97% for this reaction.
Example 3
44.6mg (0.2mmol) of 6-bromo-2-naphthol, 58.8 mg (0.2mmol) of 4-phenylmethylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, (0.01 mmol) of phosphoric acid and 1.0mL of water are introduced under nitrogen into a Schlenk tube at 100%oC stirring the reaction for 8 hours. After the reaction is finished, the target product is separated and purified by column chromatography, and the yield of the target product is 92%.
Example 4
33.8 mg (0.2mmol) of 6-cyano-2-naphthol, 58.8 mg (0.2mmol) ofmmol) 4-Phenylmethylene-2, 6-di-tert-butyl-2, 5-cyclohexadiene-1-one, (0.01 mmol) phosphoric acid and 1.0mL of water were added under nitrogen to a Schlenk tube at 100%oC stirring the reaction for 8 hours. After the reaction is finished, the target product is separated and purified by column chromatography, and the yield of the target product is 70%.
Example 5
44.6mg (0.2mmol) of 7-bromo-2-naphthol, 58.8 mg (0.2mmol) of 4-phenylmethylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, (0.01 mmol) of phosphoric acid and 1.0mL of water are introduced under nitrogen into a Schlenk tube at 100%oC stirring the reaction for 8 hours. After the reaction is finished, the target product is separated and purified by column chromatography, and the yield of the target product is 80%.
Example 6
34.8 mg (0.2mmol) of 6-methoxy-2-naphthol, 58.8 mg (0.2mmol) of 4-phenylmethylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, (0.01 mmol) of phosphoric acid and 1.0mL of water are introduced under nitrogen into a Schlenk tube at 100%oC stirring the reaction for 8 hours. . After the reaction is finished, the target product is separated and purified by column chromatography, and the yield of the target product is 90%.
Example 7
32.0mg (0.2mmol) of 2, 3-dihydroxynaphthalene, 58.8 mg (0.2mmol) of 4-phenylmethylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, (0.01 mmol) of phosphoric acid and 1.0mL of water were added under nitrogen to a Schlenk tube at 100 deg.FoC stirring the reaction for 8 hours. . After the reaction is finished, the target product is separated and purified by column chromatography, and the yield of the target product is 73%.
Example 8
40.44 mg (0.2mmol) of 6-hydroxy-2-naphthylmethyl ester, 58.8 mg (0.2mmol) of 4-phenylmethylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, (0.01 mmol) of phosphoric acid and 1.0mL of water were added under nitrogen to a Schlenk tube at 100 deg.FoC stirring the reaction for 8 hours. After the reaction is finished, the target product is separated and purified by column chromatography, and the yield of the target product is 95%.
Example 9
34.4 mg (0.2mmol) of 6-hydroxy-2-naphthaldehyde and 58.8 mg (0.2mmol) of 4-phenylmethylene-2, 6-di-tert-butyl-2, 5-cyclohexanedi-methylene are introducedEn-1-one, (0.01 mmol) phosphoric acid and 1.0mL water were added under nitrogen to a Schlenk tube at 100 deg.CoC stirring the reaction for 8 hours. After the reaction is finished, the target product is separated and purified by column chromatography, and the yield of the target product is 70%.
Example 10
37.6 mg (0.2mmol) of 6-hydroxy-2-naphthoic acid, 58.8 mg (0.2mmol) of 4-phenylmethylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, (0.01 mmol) of phosphoric acid and 1.0mL of water are introduced under nitrogen into a Schlenk tube at 100 deg.FoC stirring the reaction for 8 hours. After the reaction is finished, the target product is separated and purified by column chromatography, and the yield of the target product is 91%.
Example 11
28.8 mg (0.2mmol) of 2-naphthol, 72.44 mg (0.2mmol) of 4- (4-methylphenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, (0.01 mmol) of phosphoric acid and 1.0mL of water were added under nitrogen to a Schlenk's tube at 100 deg.FoC stirring the reaction for 8 hours. After the reaction is finished, the target product is separated and purified by column chromatography, and the yield of the target product is 99%.
Example 12
28.8 mg (0.2mmol) of 2-naphthol, 72.4 mg (0.2mmol) of 4- (3-fluorophenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, (0.01 mmol) of phosphoric acid and 1.0mL of water were added under nitrogen to a Schlenk's tube at 100. mu.LoC stirring the reaction for 8 hours. After the reaction is finished, the target product is separated and purified by column chromatography, and the yield of the target product is 87%.
Example 13
28.8 mg (0.2mmol) of 2-naphthol, 42.0 mg (0.2mmol) of 4-phenylmethylene-2, 6-dimethyl-2, 5-cyclohexadien-1-one, (0.01 mmol) of phosphoric acid and 1.0mL of water are introduced under nitrogen into a Schlenk tube at 100%oThe reaction was stirred for 8 hours at C. After the reaction is finished, the target product is separated and purified by column chromatography, and the yield of the target product is 90%.
Example 14
28.8 mg (0.2mmol) of 2-naphthol, 53.2 mg (0.2mmol) of 4-phenylmethylene-2, 6-diisopropyl-2, 5-cyclohexadiene-1-one, (0.01 mmol) of phosphoric acid and 1.0mL of water were added under nitrogenIn Schlenk tube, at 100oThe reaction was stirred for 8 hours at C. After the reaction is finished, the target product is separated and purified by column chromatography, and the yield of the target product is 96%.
Example 15
28.8 mg (0.2mmol) of 2-naphthol, 60.0 mg (0.2mmol) of 4- (2-thienyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, (0.01 mmol) of phosphoric acid and 1.0mL of water were added under nitrogen to a Schlenk tube at 100 deg.FoThe reaction was stirred for 8 hours at C. After the reaction is finished, the target product is separated and purified by column chromatography, and the yield of the target product is 92%.
It can be seen from the above examples that the method for preparing the corresponding 1-diarylmethyl substituted-2-naphthol compound containing different substituted functional groups by efficiently reacting the 2-naphthol compound with the 4-arylmethylene-2, 6-dialkyl-2, 5-cyclohexadiene-1-one compound adopted by the invention has the advantages of mild reaction conditions, environmental protection, cheap and easily available catalyst, simple preparation and the like. In addition, the method also has the advantages of wide substrate applicability, high yield and the like, and provides a method for efficiently synthesizing the 1-diarylmethyl substituted-2-naphthol compounds containing different substituted functional groups.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the present invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.

Claims (4)

1. A compound with structural formula prepared by reacting 2-naphthol compound with 4-arylmethylene-2, 6-dialkyl-2, 5-cyclohexadiene-1-ketone compound（I）The preparation method of the middle 1-diarylmethyl substituted-2-naphthol compound comprises the following steps:
Figure 718361DEST_PATH_IMAGE001
（I）
the method is characterized by comprising the following steps:
taking a reaction amount of 2-naphthol compound, 4-arylmethylene-2, 6-dialkyl-2, 5-cyclohexadiene-1-one, a catalyst and a solvent, placing the mixture in a reaction vessel under the condition of nitrogen, mixing the mixture under stirring at 25-120 DEG CoC, reacting for 8-14 hours to obtain corresponding 1-diaryl methyl substituted-2-naphthol compounds containing different substituted functional groups;
wherein,
the catalyst is selected from phosphoric acid (H)3PO4) The solvent is selected from water;
ar is selected from phenyl, 2-methylphenyl, 4-methylphenyl, 2-hydroxyphenyl, 4-ethylphenyl, 4-tert-butylphenyl, 4-isopropoxyphenyl, 4-benzyloxyphenyl, 3-methoxyphenyl, 2, 5-dimethoxyphenyl, 3-cyanophenyl, 4-trifluoromethylphenyl, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-bromophenyl group, 3-bromophenyl group, 4-bromophenyl group, 3-nitrophenyl group, 3-methoxy-4-hydroxyphenyl group, 4-aldehyde phenyl group, 2-pyridyl group, 6-benzo-2, 3-dihydrofuryl group, 2-thienyl group, 3-thienyl group;
R1is methyl, isopropyl, tert-butyl;
R2is 6-cyano, 6-bromo, 7-bromo, 6-methoxy, 3-hydroxy, 7-hydroxy, 6-carbomethoxy, 7-methoxy, 6-carboxy, 6-aldehyde group.
2. The process according to claim 1, wherein the 4-arylmethylene-2, 6-dialkyl-2, 5-cyclohexadiene-1-one is selected from the group consisting of 4-phenylmethylene-2, 6-di-tert-butyl-2, 5-cyclohexadiene-1-one, 4- (2-methylphenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadiene-1-one, 4- (4-methylphenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadiene-1-one, 4- (2-hydroxyphenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadiene-1-one, and mixtures thereof, 4- (4-ethylphenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, 4- (4-tert-butylphenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, 4- (4-isopropoxyphenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, 4- (4-benzyloxyphenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, 4- (3-methoxyphenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, and mixtures thereof, 4- (2, 5-dimethoxyphenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, 4- (3-cyanophenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, 4- (4-trifluoromethylphenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, 4- (2-fluorophenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, a salt thereof, a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable salt thereof, 4- (3-fluorophenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, 4- (4-fluorophenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, 4- (2-bromophenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, 4- (3-bromophenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, 4- (4-bromophenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, 4- (3-nitrophenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadiene-1-one, 4- (3-methoxy-4-hydroxyphenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadiene-1-one, 4- (4-formylphenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadiene-1-one, 4- (2-pyridyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadiene-1-one, 4- (6-benzo-2, 3-dihydrofuranyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadiene-1-one, mixtures thereof, 4- (2-thienyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadiene-1-one, 4- (3-thienyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadiene-1-one, 4-phenylmethylene-2, 6-dimethyl-2, 5-cyclohexadiene-1-one, 4-phenylmethylene-2, 6-diisopropyl-2, 5-cyclohexadiene-1-one.
3. The method according to claim 1, wherein the 2-naphthol compound is selected from the group consisting of 6-cyano-2-naphthol, 6-bromo-2-naphthol, 7-bromo-2-naphthol, 6-methoxy-2-naphthol, 2, 3-dihydroxynaphthalene, 2, 7-dihydroxynaphthalene, 6-hydroxy-2-naphthylmethyl ester, 7-methoxy-2-naphthol, 6-hydroxy-2-naphthoic acid and 6-hydroxy-2-naphthoic aldehyde.
4. The method according to claim 1, wherein the molar ratio of the 4-arylmethylene-2, 6-dialkyl-2, 5-cyclohexadiene-1-one compound to the 2-naphthol compound is [1:1 ]; the mol ratio of the 4-arylmethylene-2, 6-dialkyl-2, 5-cyclohexadiene-1-ketone compound to the phosphoric acid is 1: [0.01-0.2].
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CN114315528A (en) * 2022-01-21 2022-04-12 湖南理工学院 Novel method for preparing 4-dimethyl aryl substituted phenol compound by silver catalysis
CN114369011A (en) * 2022-01-21 2022-04-19 湖南理工学院 Green novel method for preparing 2-diarylmethyl substituted-1-naphthol compound
CN114369011B (en) * 2022-01-21 2024-07-09 湖南理工学院 New green method for preparing 2-diaryl methyl substituted-1-naphthol compound

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