CN112679299A - Preparation method of diarylmethane and derivatives thereof - Google Patents
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Abstract
The invention discloses a preparation method of diarylmethane compounds and derivatives thereof, wherein aryl aldehyde and aromatic hydrocarbon compounds are heated and reacted in the presence of phosphorous acid and iodine in protective atmosphere to prepare diarylmethane and derivatives thereof. The invention selects cheap green solid phosphorous acid as a reduction reagent and an accelerant for reaction, and starts from simple and easily obtained aryl aldehyde compounds in the presence of elemental iodine, the preparation of diarylmethane and derivatives thereof is efficiently realized by a one-pot one-step method, and the invention has the advantages of simple operation, cheap and easily obtained reagents, environmental protection and the like, avoids using expensive reduction reagents, metal reagents and transition metal catalysts, and is beneficial to industrial production.
Description
Technical Field
The invention relates to a preparation method of diarylmethane and derivatives thereof, belonging to the field of fine chemical synthesis.
Background
Diarylmethane and its derivatives are important organic synthetic intermediates, which have relatively complex structural units and are widely present in natural products, drug molecules and various bioactive substance molecules. In addition, the diarylmethane compounds can also be widely applied to perfumes, dyes and aromatic solvents. Therefore, the research and development of a new synthetic route of the high-efficiency green diarylmethane compound have important practical value and scientific research significance.
According to relevant documents and patent reports, the preparation of diarylmethane and derivatives thereof mainly comprises the following types:
the first method comprises the following steps: the catalyst is prepared by the traditional Friedel-crafts alkylation reaction, namely, the catalyst is prepared by taking benzyl halide or benzyl alcohol as a raw material and equivalent metal Lewis acid as an accelerant to react with aromatic hydrocarbon. However, the method has the disadvantages of excessive metal promoter, difficult post-treatment, environmental unfriendliness, poor regioselectivity and more byproducts.
And the second method comprises the following steps: prepared by the reduction reaction of diaryl ketone or diaryl methanol. However, the method needs dangerous hydrogen, sodium borohydride or expensive silicon hydrogen reagent, has difficult raw material source, difficult preparation and high cost, and is not suitable for all kinds of large-scale industrial production.
And the third is that: the diarylmethane compounds are prepared by a transition metal catalyzed coupling reaction. The method usually needs to use a coupling reagent with higher activity, such as an organic zinc reagent, a Grignard reagent or an organic boron reagent, and the like, so that the method is expensive, has air-sensitive sensitivity, has certain danger for the reagent, and undoubtedly increases the difficulty of industrial production. In addition, the introduction of the transition metal catalyst not only increases the production cost, but also greatly limits the application range of the catalyst because the residue of the metal has an important influence on the quality of the product in the post-treatment process of the reaction.
Therefore, a novel method which is cheap, green, low in toxicity and efficient is urgently needed to be developed to make up the defects of the method and provide a novel path for synthesizing the diarylmethane compound.
Disclosure of Invention
In order to solve the problems in the preparation of the existing diarylmethane and the derivatives thereof, the invention aims to provide a preparation method of diarylmethane and the derivatives thereof, which uses cheap and easily obtained phosphorous acid as a reduction reagent and uses elemental iodine as an accelerator.
In order to achieve the above object, the present invention provides a method for preparing diarylmethane and its derivatives, wherein aryl aldehyde and aromatic hydrocarbon compound are heated and reacted in the presence of phosphorous acid and iodine in a protective atmosphere to obtain diarylmethane and its derivatives, and the reaction equation is as shown in formula 1:
preferably, the aryl aldehyde is selected from one of the following structural formulas:
preferably, the aromatic hydrocarbon compound is selected from one of the following structural formulas:
preferably, the molar ratio of aryl aldehyde to aromatic compound is not higher than 1: 1, more preferably 1: 7.5 to 22.5; the molar ratio of aryl aldehyde to phosphorous acid is 1: 1-4, and more preferably 1: 2 to 2.5; the molar ratio of aryl aldehyde to iodine is 1: 0.2 to 1, and more preferably 1: 0.7 to 0.8. In the present invention, the aromatic hydrocarbon compound serves as both a reactant and a solvent, and therefore, it is preferable to add an excessive amount of the aromatic hydrocarbon compound during the reaction, so that the yield of the produced diarylmethane and its derivatives can be further improved.
Preferably, the reaction temperature is at least 50 ℃, and further preferably 50-150 ℃; the reaction time is at least 12 hours, and more preferably 12-24 hours.
Preferably, after the reaction is finished, the solution after the reaction is treated by a sodium thiosulfate aqueous solution, extracted, dried, filtered, steamed in a rotary mode, and then separated and purified through column chromatography.
The invention has the following beneficial effects:
the invention selects cheap green solid phosphorous acid as a reduction reagent and an accelerant for reaction, and starts from simple and easily obtained aryl aldehyde compounds in the presence of elemental iodine, the preparation of diarylmethane and derivatives thereof is efficiently realized by a one-pot one-step method, and the invention has the advantages of simple operation, cheap and easily obtained reagents, environmental protection and the like, avoids using expensive reduction reagents, metal reagents and transition metal catalysts, and is beneficial to industrial production.
Drawings
FIG. 1 is a nuclear magnetic hydrogen spectrum of a sample prepared in example 1;
FIG. 2 is a nuclear magnetic carbon spectrum of a sample obtained in example 1;
FIG. 3 is a nuclear magnetic hydrogen spectrum of a sample prepared in example 2;
FIG. 4 is a nuclear magnetic carbon spectrum of a sample prepared in example 2;
FIG. 5 is a nuclear magnetic hydrogen spectrum of a sample obtained in example 3;
FIG. 6 is a nuclear magnetic carbon spectrum of a sample prepared in example 3;
FIG. 7 is a nuclear magnetic hydrogen spectrum of a sample obtained in example 4;
FIG. 8 is a nuclear magnetic carbon spectrum of a sample obtained in example 4;
FIG. 9 is a nuclear magnetic hydrogen spectrum of a sample obtained in example 5;
FIG. 10 is a nuclear magnetic carbon spectrum of a sample obtained in example 5;
FIG. 11 is a nuclear magnetic hydrogen spectrum of a sample obtained in example 6;
FIG. 12 is a nuclear magnetic carbon spectrum of a sample obtained in example 6;
FIG. 13 is a nuclear magnetic hydrogen spectrum of a sample obtained in example 7;
FIG. 14 is a nuclear magnetic carbon spectrum of a sample obtained in example 7; ,
FIG. 15 is a nuclear magnetic hydrogen spectrum of a sample obtained in example 8;
FIG. 16 is a nuclear magnetic carbon spectrum of a sample prepared in example 8;
FIG. 17 is a nuclear magnetic hydrogen spectrum of a sample obtained in example 9;
FIG. 18 is a nuclear magnetic carbon spectrum of a sample obtained in example 9;
FIG. 19 is a nuclear magnetic hydrogen spectrum of a sample obtained in example 10;
FIG. 20 is a nuclear magnetic carbon spectrum of a sample obtained in example 10;
FIG. 21 is a nuclear magnetic hydrogen spectrum of a sample obtained in example 11;
FIG. 22 is a nuclear magnetic carbon spectrum of a sample obtained in example 11;
FIG. 23 is a nuclear magnetic hydrogen spectrum of a sample obtained in example 12;
FIG. 24 is a nuclear magnetic carbon spectrum of a sample obtained in example 12;
FIG. 25 is a nuclear magnetic hydrogen spectrum of a sample obtained in example 13;
FIG. 26 is a nuclear magnetic carbon spectrum of a sample obtained in example 13;
FIG. 27 is a nuclear magnetic hydrogen spectrum of a sample obtained in example 14;
FIG. 28 is a nuclear magnetic carbon spectrum of a sample prepared in example 14;
FIG. 29 is a nuclear magnetic hydrogen spectrum of a sample obtained in example 15;
FIG. 30 is a nuclear magnetic carbon spectrum of a sample prepared in example 15;
FIG. 31 is a nuclear magnetic hydrogen spectrum of a sample prepared in example 16;
FIG. 32 is a nuclear magnetic carbon spectrum of a sample prepared in example 16;
Detailed Description
The following examples are intended to further illustrate the present invention, but not to limit the scope of the claims of the present invention.
All the raw materials are commercially available products unless otherwise specified.
Example 1
Benzaldehyde (0.6mmol), iodine (0.42mmol), phosphorous acid (1.5mmol) and mesitylene (8.63mmol) were added to a reaction flask under a nitrogen atmosphere, and the mixture was stirred at 60 ℃ for 24 hours. After the reaction is finished, Na with the mass fraction of 5 percent is added into the reaction liquid2S2O3Extracting the water solution with ethyl acetate, drying the organic phase, filtering, spin-drying, and separating by column chromatography to obtain the product. The product obtained was a colorless oily liquid
The yield thereof was found to be 93%.
1H NMR(500MHz CDCl3):δ7.16–7.13(m,2H),7.08–7.05(m,1H),6.93(d,J＝7.5Hz,2H),6.81(s,2H),3.94(s,2H),2.21(s,3H),2.12(s,6H)；
13C NMR(125MHz CDCl3):δ140.16,137.07,135.70,133.83,128.93,128.38,127.90,125.70,34.75,20.96,20.18。
Example 2
4-methylbenzaldehyde (0.6mmol), iodine (0.42mmol), phosphorous acid (1.5mmol) and mesitylene (8.63mmol) were charged in a reaction flask under a nitrogen atmosphere, and the reaction was stirred at 60 ℃ for 24 hours. After the reaction is finished, Na with the mass fraction of 5 percent is added into the reaction liquid2S2O3Aqueous solution of acetic acid ethyl esterExtracting ester, drying organic phase, filtering, spin drying, and separating by column chromatography to obtain the final product. The product obtained was a colorless oily liquid
The yield thereof was found to be 91%.
1H NMR(500MHz CDCl3):δ7.08(d,J＝7.5Hz,2H),6.95–6.93(m,4H),4.02(s,2H),2.33(s,6H),2.24(s,6H)；
13C NMR(125MHz CDCl3):δ137.04,137.01,135.59,135.11,134.04,129.08,128.90,127.77,34.32,21.00,20.95,20.15。
Example 3
2-methylbenzaldehyde (0.6mmol), iodine (0.42mmol), phosphorous acid (1.5mmol) and mesitylene (8.63mmol) were charged in a reaction flask under a nitrogen atmosphere, and the reaction was stirred at 60 ℃ for 24 hours. After the reaction is finished, Na with the mass fraction of 5 percent is added into the reaction liquid2S2O3Extracting the water solution with ethyl acetate, drying the organic phase, filtering, spin-drying, and separating by column chromatography to obtain the product. The product obtained was a white solid
The yield thereof was found to be 87%.
1H NMR(500MHz CDCl3):δ7.20(d,J＝7.5Hz,1H),7.10(t,J＝7.5Hz,1H),7.00(t,J＝7.5Hz,1H),6.94(s,2H),6.53(d,J＝8.0Hz,1H),3.89(s,2H),2.45(s,3H),2.34(s,3H),2.17(s,6H)；
13C NMR(125MHz CDCl3):δ137.96,137.21,136.26,135.63,133.57,129.67,128.86,126.24,126.09,125.71,32.01,20.97,19.90,19.80。
Example 4
2, 6-dimethyl-benzaldehyde (0.6mmol), iodine (0.48mmol), phosphorous acid (1.2mmol) and mesitylene (8.63mmol) were charged in a reaction flask under nitrogen atmosphere, and the mixture was stirred at 60 ℃ for 24 hours. After the reaction is finished, Na with the mass fraction of 5 percent is added2S2O3Aqueous solution, extraction with ethyl acetate, organicAnd (4) drying, filtering, spin-drying and separating by column chromatography to obtain the product. The product obtained was a white solid
The yield thereof was found to be 60%.
1H NMR(500MHz CDCl3):δ7.06–7.03(m,1H),7.00–6.98(m,2H),6.83(s,2H),4.07(s,2H),2.28(s,3H),2.16(s,6H),2.11(s,6H)；
13C NMR(125MHz CDCl3):δ138.09,136.90,136.72,135.04,134.61,129.40,128.56,125.69,31.42,20.95,20.85,20.77。
Example 5
4-Tert-butylbenzaldehyde (0.6mmol), iodine (0.42mmol), phosphorous acid (1.5mmol) and mesitylene (8.63mmol) were charged to a reaction flask under a nitrogen atmosphere, and the mixture was stirred at 60 ℃ for 24 hours. After the reaction is finished, Na with the mass fraction of 5 percent is added into the reaction liquid2S2O3Extracting the water solution with ethyl acetate, drying the organic phase, filtering, spin-drying, and separating by column chromatography to obtain the product. The product obtained was a white solid
The yield thereof was found to be 89%.
1H NMR(500MHz CDCl3):δ7.28–7.26(m,2H),6.97(d,J＝8.0Hz,2H),6.91(s,2H),4.01(s,2H),2.31(s,3H),2.24(s,6H),1.31(s,9H)；
13C NMR(125MHz CDCl3):δ148.41,136.98,136.97,135.54,134.14,128.85,127.51,125.21,34.30,34.21,31.41,20.92,20.21。
Example 6
P-phenylbenzaldehyde (0.6mmol), iodine (0.42mmol), phosphorous acid (1.5mmol) and mesitylene (8.63mmol) were charged to a reaction flask under nitrogen atmosphere, and the reaction was stirred at 60 ℃ for 24 hours. After the reaction is finished, Na with the mass fraction of 5 percent is added into the reaction liquid2S2O3Extracting the water solution with ethyl acetate, drying the organic phase, filtering, spin-drying, and separating by column chromatographyAnd (5) separating to obtain a product. The product obtained was a white solid
The yield thereof was found to be 93%.
1H NMR(500MHz CDCl3):δ7.60(d,J＝8.0Hz,2H),7.51(d,J＝8.0Hz,2H),7.45(t,J＝8.0Hz,2H),7.37–7.34(m,1H),7.13(d,J＝7.5Hz,2H),6.96(s,2H),4.11(s,2H),2.35(s,3H),2.29(s,6H)；
13C NMR(125MHz CDCl3):δ141.13,139.32,138.71,137.08,135.79,133.76,129.00,128.75,128.32,127.14,127.04,127.01,34.44,20.99,20.24。
Example 7
P-fluorobenzaldehyde (0.6mmol), iodine (0.42mmol), phosphorous acid (1.5mmol) and mesitylene (8.63mmol) were added to a reaction flask under a nitrogen atmosphere, and the reaction was stirred at 60 ℃ for 24 hours. After the reaction is finished, Na with the mass fraction of 5 percent is added into the reaction liquid2S2O3Extracting the water solution with ethyl acetate, drying the organic phase, filtering, spin-drying, and separating by column chromatography to obtain the product. The product obtained was a colorless oily liquid
The yield thereof was found to be 89%.
1H NMR(500MHz CDCl3):δ6.98–6.90(m,6H),3.98(s,2H),2.30(s,3H),2.20(s,6H)；
13C NMR(125MHz CDCl3):δ161.18(d,J＝242Hz),136.93,135.86,135.64(d,J＝2.9Hz),133.65,129.12(d,J＝7.6Hz),128.98,115.1(d,J＝20.9Hz),33.89,20.92,20.09。
Example 8
P-chlorobenzaldehyde (0.6mmol), iodine (0.42mmol), phosphorous acid (1.5mmol) and mesitylene (8.63mmol) were charged into a reaction flask under nitrogen atmosphere, and the reaction was stirred at 60 ℃ for 24 hours. After the reaction is finished, Na with the mass fraction of 5 percent is added into the reaction liquid2S2O3Extracting the aqueous solution with ethyl acetate, drying and filtering the organic phase,and (4) after spin-drying, carrying out column chromatography separation to obtain a product. The product obtained was a white solid
The yield thereof was found to be 80%.
1H NMR(500MHz CDCl3):δ7.21–7.18(m,2H),6.94(d,J＝8.5Hz,2H),6.90(s,2H),3.98(s,2H),2.30(s,3H),2.19(s,6H)；
13C NMR(125MHz CDCl3):δ138.61,136.94,135.95,133.25,131.39,129.17,128.99,128.45,34.07,20.92,20.09。
Example 9
P-bromobenzaldehyde (0.6mmol), iodine (0.42mmol), phosphorous acid (1.5mmol) and mesitylene (8.63mmol) were added to a reaction flask under a nitrogen atmosphere, and the mixture was stirred at 60 ℃ for 24 hours. After the reaction is finished, Na with the mass fraction of 5 percent is added into the reaction liquid2S2O3Extracting the water solution with ethyl acetate, drying the organic phase, filtering, spin-drying, and separating by column chromatography to obtain the product. The product obtained was a white solid
The yield thereof was found to be 85%.
1H NMR(500MHz CDCl3):δ7.36–7.35(m,2H),6.91–6.89(m,4H),3.97(s,2H),2.31(s,3H),2.20(s,6H)；
13C NMR(125MHz CDCl3):δ139.17,136.95,135.98,133.17,131.41,129.61,129.02,119.43,34.15,20.94,20.10。
Example 10
Methyl p-formylbenzoate (0.6mmol), iodine (0.48mmol), phosphorous acid (1.2mmol) and mesitylene (8.63mmol) were charged into a reaction flask under a nitrogen atmosphere, and the reaction was stirred at 60 ℃ for 24 hours. After the reaction is finished, Na with the mass fraction of 5 percent is added into the reaction liquid2S2O3Extracting the water solution with ethyl acetate, drying the organic phase, filtering, spin-drying, and separating by column chromatography to obtain the product. The product obtained was a white solid
The yield thereof was found to be 52%.
1H NMR(500MHz CDCl3):δ7.92–7.89(m,2H),7.08(d,J＝8.5Hz,2H),6.91(s,2H),4.06(s,2H),3.89(s,3H),2.30(s,3H),2.19(s,6H)；
13C NMR(125MHz CDCl3):δ167.16,145.87,136.99,136.06,132.94,129.74,129.02,127.87,127.80,51.99,34.87,20.93,20.14。
Example 11
P-trifluoromethylbenzaldehyde (0.6mmol), iodine (0.42mmol), phosphorous acid (1.5mmol) and mesitylene (8.63mmol) were charged in a reaction flask under nitrogen atmosphere, and the reaction was stirred at 60 ℃ for 24 hours. After the reaction is finished, Na with the mass fraction of 5 percent is added into the reaction liquid2S2O3Extracting the water solution with ethyl acetate, drying the organic phase, filtering, spin-drying, and separating by column chromatography to obtain the product. The product obtained was a white solid
The yield thereof was found to be 95%.
1H NMR(500MHz CDCl3):δ7.49(d,J＝8.5Hz,2H),7.13(d,J＝8.0Hz,2H),6.92(s,2H),4.07(s,2H),2.31(s,3H),2.20(s,6H)；
13C NMR(125MHz CDCl3):δ144.44,136.95,136.17,132.76,129.07,128.14(t,J＝32.0Hz),128.12,125.29(t,J＝3.8Hz),124.36(t,J＝270.0Hz),34.60,20.92,20.10。
Example 12
3, 4-dichloro-benzaldehyde (0.6mmol), iodine (0.42mmol), phosphorous acid (1.5mmol) and mesitylene (8.63mmol) were charged in a reaction flask under nitrogen atmosphere, and the mixture was stirred at 60 ℃ for 24 hours. After the reaction is finished, Na with the mass fraction of 5 percent is added into the reaction liquid2S2O3Extracting the water solution with ethyl acetate, drying the organic phase, filtering, spin-drying, and separating by column chromatography to obtain the product. The product obtained was a colorless oily liquid
The yield thereof was found to be 81%.
1H NMR(500MHz CDCl3):δ7.30(d,J＝8.0Hz,1H),7.11(s,1H),6.92(s,2H),6.85(d,J＝8.0Hz,1H),3.98(s,2H),2.32(s,3H),2.20(s,6H)；
13C NMR(125MHz CDCl3):δ140.62,136.88,136.26,132.46,132.40,130.26,129.75,129.69,129.15,127.30,33.91,20.95,20.11。
Example 13
3-methyl-4-fluoro-benzaldehyde (0.6mmol), iodine (0.42mmol), phosphorous acid (1.5mmol) and mesitylene (8.63mmol) were charged in a reaction flask under nitrogen atmosphere, and the reaction was stirred at 60 ℃ for 24 hours. After the reaction is finished, Na with the mass fraction of 5 percent is added into the reaction liquid2S2O3Extracting the water solution with ethyl acetate, drying the organic phase, filtering, spin-drying, and separating by column chromatography to obtain the product. The product obtained was a colorless oily liquid
The yield thereof was found to be 80%.
1H NMR(500MHz CDCl3):δ6.96(s,2H),6.93–6.89(m,2H),6.82–6.80(m,1H),4.01(s,2H),2.36(s,3H),2.27(s,9H)；
13C NMR(125MHz CDCl3):δ159.79(d,J＝240.6Hz),136.98,135.79,135.37(d,J＝3.5Hz),133.83,130.74(d,J＝4.9Hz),129.02,126.39(d,J＝7.6Hz),124.51(d,J＝17.0Hz),114.74(d,J＝22.0Hz),33.97,20.97,20.16,14.63(d,J＝3.6Hz)。
Example 14
Benzaldehyde (0.6mmol), iodine (0.42mmol), phosphorous acid (1.5mmol) and benzene (13.5mmol) were added to a reaction flask under a nitrogen atmosphere, and the mixture was stirred at 60 ℃ for 24 hours. After the reaction is finished, Na with the mass fraction of 5 percent is added into the reaction liquid2S2O3Extracting the aqueous solution with ethyl acetate, drying the organic phase, filtering, spin-drying the solvent, and passing through the column layerSeparating and separating to obtain the product. The product obtained was a colorless oily liquid
The yield thereof was found to be 40%.
1H NMR(500MHz CDCl3):δ7.32–7.29(m,4H),7.23–7.21(m,6H),4.01(s,2H)；
13C NMR(125MHz CDCl3):δ141.15,128.97,128.48,126.09,41.97。
Example 15
Benzaldehyde (0.6mmol), iodine (0.48mmol), phosphorous acid (1.2mmol) and toluene (11.3mmol) were added to a reaction flask under a nitrogen atmosphere, and the reaction was stirred at 60 ℃ for 24 hours. After the reaction is finished, Na with the mass fraction of 5 percent is added into the reaction liquid2S2O3Extracting the water solution with ethyl acetate, drying and filtering the organic phase, spin-drying the solvent, and finally separating by column chromatography to obtain the product. The product obtained was a colorless oily liquid
The yield thereof was found to be 50%.
1H NMR(500MHz CDCl3):δ7.19–7.15(m,4.47H),7.09–6.97(m,15.22H),3.89(s,2H),3.84(s,2.59H),2.21(s,3.93H),2.14(s,3H)；
13C NMR(125MHz CDCl3):δ141.51,140.49,139.02,138.17,136.72,135.62,130.38,130.05,129.25,128.97,128.91,128.84,128.52,128.48,126.55,126.09,126.07,126.01,41.61,39.55,21.11,19.76。
Example 16
Benzaldehyde (0.6mmol), iodine (0.48mmol), phosphorous acid (1.2mmol) and phenol (4.6mmol) were added to a reaction flask under a nitrogen atmosphere, and the reaction was stirred at 60 ℃ for 24 hours. After the reaction is finished, Na with the mass fraction of 5 percent is added into the reaction liquid2S2O3Extracting the water solution with ethyl acetate, drying and filtering the organic phase, spin-drying the solvent, and finally separating by column chromatography to obtain the product. The product obtained was a colorless oily liquid
The yield thereof was found to be 40%.
1H NMR(500MHz CDCl3):δ7.34–7.30(m,2H),7.27–7.23(m,3H),7.17–7.13(m,2H),6.94–6.90(m,1H),6.81–6.79(m,1H),4.02(s,2H)；
13C NMR(125MHz CDCl3):δ153.75,139.96,131.03,128.75,128.67,127.86,127.06,126.38,120.97,115.74,36.35。
Claims (8)
1. A preparation method of diarylmethane and its derivatives is characterized in that: in a protective atmosphere, heating aryl aldehyde and an aromatic hydrocarbon compound to react in the presence of phosphorous acid and iodine simple substances to prepare diarylmethane and derivatives thereof, wherein the reaction equation is shown as formula 1:
2. the method for preparing diarylmethane and its derivatives according to claim 1, wherein: the aryl aldehyde is selected from one of the following structural formulas:
3. the method for preparing diarylmethane and its derivatives according to claim 1, wherein: the aromatic hydrocarbon compound is selected from one of the following structural formulas:
4. the method for preparing diarylmethane and its derivatives according to claim 1, wherein: the molar ratio of aryl aldehyde to aromatic compound is not higher than 1: 1; the molar ratio of aryl aldehyde to phosphorous acid is 1: 1-4; the molar ratio of aryl aldehyde to iodine is 1: 0.2 to 1.
5. The method for preparing diarylmethane and its derivatives according to claim 4, wherein: the molar ratio of the aryl aldehyde to the aromatic hydrocarbon compound is 1: 7.5 to 22.5; the molar ratio of aryl aldehyde to phosphorous acid is 1: 2 to 2.5; the molar ratio of aryl aldehyde to iodine is 1: 0.7 to 0.8.
6. The method for preparing diarylmethane and its derivatives according to claim 1, wherein: the reaction temperature is at least 50 ℃, and the reaction time is at least 12 h.
7. The method for preparing diarylmethane and its derivatives according to claim 6, wherein: the reaction temperature is 50-150 ℃; the reaction time is 12-24 h.
8. The method for preparing diarylmethane and its derivatives according to claim 1, wherein: after the reaction is finished, treating the reaction solution by using a sodium thiosulfate aqueous solution, extracting, drying, filtering, carrying out rotary evaporation, and then separating and purifying by using column chromatography.
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| CN116023200A (en) * | 2022-01-27 | 2023-04-28 | 浙江扬帆新材料股份有限公司 | Method for preparing methylene compound by reduction of aromatic aldehyde (ketone) compound |
| CN116023200B (en) * | 2022-01-27 | 2023-07-25 | 江西扬帆新材料有限公司 | Method for preparing methylene compound by reduction of aromatic aldehyde (ketone) compound |
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