CN114369011A - Green novel method for preparing 2-diarylmethyl substituted-1-naphthol compound - Google Patents

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

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CN114369011A
CN114369011A CN202210072586.7A CN202210072586A CN114369011A CN 114369011 A CN114369011 A CN 114369011A CN 202210072586 A CN202210072586 A CN 202210072586A CN 114369011 A CN114369011 A CN 114369011A
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tert
butyl
methylene
cyclohexadiene
cyclohexadien
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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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Hunan Institute of Science and Technology
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
    • C07C37/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by addition reactions, i.e. reactions involving at least one carbon-to-carbon unsaturated bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms

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Abstract

The invention provides a method for efficiently and selectively synthesizing 2-diaryl methyl substituted-1-naphthol compounds containing different substituted functional groups, which adopts phosphoric acid as a catalyst, 1-naphthol compounds and 4-arylmethylene-2, 6-dialkyl-2, 5-cyclohexadiene-1-ketone compounds as reaction substrates, and a reaction system takes water as a solvent. 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 high. 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 2-diaryl methyl substituted-1-naphthol compound, and has good industrial application prospect. The invention also provides corresponding 2-diarylmethyl substituted-1-naphthol compounds containing different substituted functional groups.

Description

Green novel method for preparing 2-diarylmethyl substituted-1-naphthol compound
Technical Field
The invention relates to the field of application catalytic synthesis of 2-diarylmethyl substituted-1-naphthol compounds, in particular to a novel method for preparing 2-diarylmethyl substituted-1-naphthol compounds by efficiently reacting 1-naphthol compounds with 4-arylmethylene-2, 6-dialkyl-2, 5-cyclohexadiene-1-ketone compounds.
Background
2-diaryl methyl substituted-1-naphthol compounds and derivatives thereof are important organic compounds and have wide application in the aspects of medical intermediates, pesticide synthesis, biological probes, photovoltaic cells, polymeric materials, asymmetric catalysis and the like.
The method for synthesizing 2-alkyl/aryl substituted-1-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 1-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 2-position C-H bonds of 1-naphthol to prepare the corresponding 2-alkyl/aryl substituted-1-naphthol compound; but the selectivity in the reaction process is poor, and the defects that special ligands (carbene or organic phosphine and the like) need to be adopted, the preparation process of the catalyst is complicated, the catalyst is expensive and difficult to recycle, the reaction condition is harsh, the product is low, the functional group compatibility is poor and the like exist.
So far, no efficient synthesis method of 2-diaryl methyl substituted-1-naphthol compound is reported, and the reported synthesis method of the 2-alkyl/aryl substituted-1-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 in production at present, and partial products of the 1-naphthol compound in China mainly depend on import at present.
Aiming at the defects of the existing synthesis process of the 1-naphthol compound and the derivative thereof, the industry is focusing on developing a novel method for preparing the corresponding 2-diarylmethyl substituted-1-naphthol compound by using a stable, cheap and easily obtained 1-naphthol compound as a synthesis building block through high-efficiency catalysis by using a cheap catalyst.
Disclosure of Invention
The invention aims to provide a novel method for synthesizing a corresponding 2-diarylmethyl-substituted-1-naphthol compound by taking a cheap and easily-obtained 1-naphthol compound and a 4-arylmethylene-2, 6-dialkyl-2, 5-cyclohexadiene-1-one compound as raw materials in high efficiency and high selectivity so as to overcome the defects in the prior art.
The invention comprises the following steps: taking 1-naphthol compound, 4-arylmethylene-2, 6-dialkyl-2, 5-cyclohexadiene-1-ketone, catalyst and solvent in reaction amount, placing in a reaction vessel under nitrogen condition, mixing, and reacting for 8-14 hours at 25-120 ℃ under stirring to obtain corresponding 2-diarylmethyl substituted-1-naphthol compound containing different substituted functional groups. The specific reaction formula is as follows:
Figure DEST_PATH_IMAGE001
（I）
wherein the content of the first and second substances,
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 4-hydroxy, 4-chloro, 4-bromo, 4-nitro, 4-methoxy, 6-methoxy;
in the above method for synthesizing 2-diarylmethyl-substituted-1-naphthol from 1-naphthol and 4-arylmethylene-2, 6-dialkyl-2, 5-cyclohexadiene-1-ones, 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, 2-tert-butyl-2, 5-cyclohexadien-one, 2-methyl-1-one, 2-tert-butyl-one, 5-cyclohexadien-one, 2-tert-butyl-one, 5-methyl-one, 2-methyl-one, 2-butyl-methyl-one, 2-methyl-ethyl-methyl-one, 2-butyl-1-one, 2-ethyl-butyl-methyl-one, 2-ethyl-methyl-ethyl-methyl-one, 2-ethyl-methyl-ethyl, 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 2-diarylmethyl-substituted-1-naphthol from 1-naphthol and 4-arylmethylene-2, 6-dialkyl-2, 5-cyclohexadiene-1-one compound, the 1-naphthol is selected from 1, 4-dihydroxynaphthalene and 4-chloronaphthalene-1-naphthol, 4-bromo-1-naphthol, 4-nitro-1-naphthol, 4-methoxy-1-naphthol, 6-methoxy-1-naphthol.
In the method for synthesizing the 2-diarylmethyl-substituted-1-naphthol compound by using the 1-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 1-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 2-diaryl methyl substituted-1-naphthol compound from the 1-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 ] embodiments
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 (0.2 mmol) of 1-naphthol, 58.8 mg (0.2 mmol) 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 1.0 mL 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 93%.
Example 2
28.8 mg (0.2 mmol) of 1-naphthol, 58.8 mg (0.2 mmol) of 4-phenylmethylene-2, 6-di-tert-butyl-2, 5-cyclohexadiene-1-one, (0.01 mmol) of phosphoric acid and 1.0 mL 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 93% for this reaction.
Example 3
28.8 mg (0.2 mmol) of 1-naphthol, 61.6 mg (0.2 mmol) of 4- (2-methylphenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, (0.01 mmol) of phosphoric acid and 1.0 mL 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 90%.
Example 4
28.8 mg (0.2 mmol) of 1-naphthol, 62.0 mg (0.2 mmol) of 4- (2-hydroxyphenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, (0.01 mmol) of phosphoric acid and 1.0 mL of water were charged under nitrogen into a Schlenk 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 89%.
Example 5
28.8 mg (0.2 mmol) of 1-naphthol, 62.4 mg (0.2 mmol) of 4- (4-fluorophenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, (0.01 mmol) of phosphoric acid and 1.0 mL 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 89%.
Example 6
28.8 mg (0.2 mmol) of 1-naphthol, 63.8 mg (0.2 mmol) of 4- (4-cyanophenyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, (0.01 mmol) of phosphoric acid and 1.0 mL 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 85%.
Example 7
28.8 mg (0.2 mmol) of 1-naphthol, 60.0 mg (0.2 mmol) of 4- (3-thienyl) methylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, (0.01 mmol) of phosphoric acid and 1.0 mL 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
28.8 mg (0.2 mmol) of 1-naphthol, 53.6 mg (0.2 mmol) of 4-phenylmethylene-2, 6-diisopropyl-2, 5-cyclohexadiene-1-one, (0.01 mmol) of phosphoric acid and 1.0 mL of water were added under nitrogen to a Schlenk tube at 100. mu.moC 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 9
28.8 mg (0.2 mmol) of 1-naphthol, 42.0 mg (0.2 mmol) of 4-phenylmethylene-2, 6-dimethyl-2, 5-cyclohexadien-1-one, (0.01 mmol) of phosphoric acid and 1.0 mL 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 product is separated and purified by column chromatography,the yield of the desired product was 76%.
Example 10
32.01 mg (0.2 mmol) of 1, 4-dihydroxynaphthalene, 58.8 mg (0.2 mmol) of 4-phenylmethylene-2, 6-di-tert-butyl-2, 5-cyclohexadiene-1-one, (0.01 mmol) of phosphoric acid and 1.0 mL of water were charged 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 85%.
Example 11
35.6 mg (0.2 mmol) of 4-chloro-1-Naphthol, 58.8 mg (0.2 mmol) of 4-phenylmethylene-2, 6-di-tert-butyl-2, 5-cyclohexadiene-1-one, (0.01 mmol) phosphoric acid and 1.0 mL of 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 83 percent.
Example 12
44.4 mg (0.2 mmol) of 4-bromo-1-naphthol, 58.8 mg (0.2 mmol) of 4-phenylmethylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, (0.01 mmol) of phosphoric acid and 1.0 mL 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 90%.
Example 13
37.8 mg (0.2 mmol) of 4-nitro-1-naphthol, 58.8 mg (0.2 mmol) of 4-phenylmethylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, (0.01 mmol) of phosphoric acid and 1.0 mL of water were added under nitrogen to a Schlenk tube at 100AoC 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 85%.
Example 14
34.8 mg (0.2 mmol) of 6-methoxy-1-naphthol, 58.8 mg (0.2 mmol) of 4-phenylmethylene-2, 6-di-tert-butyl-2, 5-cyclohexadien-1-one, (0.01 mmol) of phosphoric acid and 1.0 mL 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 81%.
It can be seen from the above examples that the method for preparing the corresponding 2-diarylmethyl substituted-1-naphthol compound containing different substituted functional groups by efficiently reacting the 1-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 2-diarylmethyl substituted-1-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 1-naphthol compound with 4-arylmethylene-2, 6-dialkyl-2, 5-cyclohexadiene-1-ketone compound（I）The preparation method of the 2-diarylmethyl substituted-1-naphthol compound comprises the following steps:
Figure DEST_PATH_IMAGE002
（I）
the method is characterized by comprising the following steps:
taking a reaction amount of 1-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 2-diaryl methyl substituted-1-naphthol compounds containing different substituted functional groups;
wherein the content of the first and second substances,
the above-mentionedThe 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 4-hydroxy, 4-chloro, 4-bromo, 4-nitro, 4-methoxy, 6-methoxy.
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 1-naphthol compound is selected from the group consisting of 1, 4-dihydroxynaphthalene, 4-chloro-1-naphthol, 4-bromo-1-naphthol, 4-nitro-1-naphthol, 4-methoxy-1-naphthol, and 6-methoxy-1-naphthol.
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 1-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].
CN202210072586.7A 2022-01-21 2022-01-21 Green novel method for preparing 2-diarylmethyl substituted-1-naphthol compound Pending CN114369011A (en)

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CN115368218A (en) * 2022-09-14 2022-11-22 湖南理工学院 Method for preparing 4-diaryl methyl substituted phenol compound
CN115925527A (en) * 2023-01-06 2023-04-07 湖南理工学院 Method for preparing alpha-diaryl methyl substituted ketone compound

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CN115368218A (en) * 2022-09-14 2022-11-22 湖南理工学院 Method for preparing 4-diaryl methyl substituted phenol compound
CN115368218B (en) * 2022-09-14 2024-01-02 湖南理工学院 Method for preparing 4-diaryl methyl substituted phenol compound
CN115925527A (en) * 2023-01-06 2023-04-07 湖南理工学院 Method for preparing alpha-diaryl methyl substituted ketone compound
CN115925527B (en) * 2023-01-06 2024-02-09 湖南理工学院 Method for preparing alpha-diaryl methyl substituted ketone compound

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