CN111393253B - Synthesis method of compound containing trans-substituted cyclohexyl - Google Patents
Synthesis method of compound containing trans-substituted cyclohexyl Download PDFInfo
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Abstract
The invention belongs to the technical field of organic synthesis, and discloses a synthesis method of a compound containing trans-substituted cyclohexyl. The invention uses cyclohexanol compound with substituent as raw material to react with organic silane and weakened Lewis acid, to obtain trans-substituted cyclohexyl compound with high selectivity. Compared with the similar method, the method has fewer byproducts and higher yield of the target product.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and discloses a synthesis method of a compound containing trans-substituted cyclohexyl.
Background
Compounds containing trans-substituted cyclohexyl groups, which are a large class of liquid crystal materials; about 70% of the liquid crystal material varieties all contain trans-substituted cyclohexyl; also has certain application in medical intermediate. The synthesis method of the compound containing the trans-substituted cyclohexyl mainly comprises the following three steps:
firstly, removing one molecule of water from cyclohexanol compound containing substituent groups to generate alkene compound (generally a mixture of various isomers and alkenes); then the alkene is hydrogenated to obtain a mixture of compounds (isomers) containing cis-substituted cyclohexyl and trans-substituted cyclohexyl, and the reaction equation of the mixture is as follows:
the first method has the advantages that the two steps of reaction of removing the molecular water and hydrogenation are relatively environment-friendly, and three wastes which are difficult to treat are avoided. The disadvantage is that the proportion of the compound containing trans-substituted cyclohexyl in the hydrogenated product is generally only 40-60%, and the rest is isomer containing cis-substituted cyclohexyl; the yield after purification can only reach 20-40%, the yield is low and the cost is high.
And secondly, reacting the cyclohexanol compound containing the substituent with organosilane and Lewis acid to obtain a mixture of compounds (isomers) containing cis-form and trans-form substituted cyclohexyl in one step. The general formula of the reaction equation is as follows:
the second method has the advantages that the process route is short, and the proportion of the compound containing the trans-substituted cyclohexyl in the product can reach 70-85%; the yield after purification can reach 60-75%. The second method has the defects that Lewis acid can cause the substituted cyclohexyl compound to generate carbocation, generate rearrangement and isomerization side reactions, and finally become various isomerization impurities which are difficult to purify and remove, thereby causing the yield reduction and the cost increase of the subsequent product purification process; even when the process conditions such as the properties of the raw materials and the degree of fluctuation in the reaction temperature are unstable, most of the raw materials and the objective product are converted into the isomerized impurities in a normal reaction time.
And thirdly, taking a mixture of compounds (isomers) containing cis-substituted cyclohexyl and trans-substituted cyclohexyl as raw materials, converting more cis-substituted cyclohexyl compounds into trans-substituted cyclohexyl compounds through some chemical reactions (generally called cyclohexyl transposition reactions), and then purifying. Many studies have been made on the method III, such as a patent publication No. CN1304914A, a patent publication No. CN102101815A, and a patent publication No. CN 102408284A. The third method has the defects that the required raw materials are products from the first method or the second method; or mother liquor after purification of the product from process one or process two; therefore, it can only be used as a supplement to the first method or the second method, but cannot replace the first method or the second method.
Disclosure of Invention
The object of the present invention is the synthesis of compounds containing trans-substituted cyclohexyl groups.
The technical scheme of the invention is as follows: a synthetic method of a compound containing trans-substituted cyclohexyl is characterized by comprising the following synthetic processes:
step 1, adding a certain amount of solvent into a container, and weakening Lewis acid;
the solvent in the step 1 is one or more of dichloromethane, chloroform, carbon tetrachloride, petroleum ether, cyclohexane, methylcyclohexane, benzene, toluene, xylene, chlorobenzene, bromobenzene, acetonitrile, nitromethane, nitrobenzene, decahydronaphthalene, tetrahydrofuran, methyl cyclopentyl ether, dioxane and methyl tert-butyl ether;
the weakened Lewis acid in the step 1 is one or a mixture of more of tetramethylammonium tetrafluoroborate, tetraethylammonium tetrafluoroborate, trimethylammonium trifluoroacetate, triethylammonium trifluoroacetate, trimethylammonium methanesulfonate, triethylammonium methanesulfonate, trimethylammonium trifluoromethanesulfonate, triethylammonium trifluoromethanesulfonate, lithium tetrachloroaluminate, sodium tetrachloroaluminate, potassium tetrachloroaluminate, tetramethylammonium tetrachloroaluminate and tetraethylammonium tetrachloroaluminate;
step 2, adding a certain amount of organosilane while stirring, and then adjusting the temperature of the reaction liquid to a preset range; then adding a certain amount of cyclohexanol compounds containing substituent groups, and carrying out heat preservation reaction for a preset time to obtain a product mainly containing a compound containing trans-substituted cyclohexyl;
2, the organosilane is one or more of trimethylsilane, triethylsilane, triisopropylsilane, tri-tert-butylsilane and trichlorosilane; the amount of organosilane is 110-300% equivalent (amount of substance) of cyclohexanol compound containing substituent; however, when the cyclohexanol compound containing substituent contains 2 or more than 2 hydroxyl groups to be reacted, the amount of organosilane used should be increased in equal proportion;
adjusting the temperature of the reaction solution and the temperature of the heat preservation reaction in the step 2 to be-20-50 ℃; keeping the temperature for reaction for 1 to 30 hours;
the dosage of the solvent in the step 1 is 100-1000% of the mass ratio of the cyclohexanol compound containing the substituent in the step 2;
the dosage of the weakened Lewis acid in the step 1 is 33 to 200 percent of equivalent (amount of substance) ratio of the cyclohexanol compound containing the substituent in the step 2; when the cyclohexanol compound containing the substituent group in the step 2 contains 2 or more hydroxyl groups needing to participate in the reaction, the dosage of the weakened Lewis acid is increased in equal proportion;
the general formula of the reaction equation is as follows:
A synthetic method of a compound containing trans-substituted cyclohexyl is characterized by comprising the following synthetic processes:
step 1, adding a certain amount of solvent and a Lewis acid weakening agent into a container, controlling the temperature to a certain temperature, slowly adding a certain amount of Lewis acid while stirring, keeping the temperature and stirring for a preset time after the addition is finished, and then cooling to be close to room temperature;
the solvent in the step 1 is one or more of dichloromethane, chloroform, carbon tetrachloride, petroleum ether, cyclohexane, methylcyclohexane, benzene, toluene, xylene, chlorobenzene, bromobenzene, acetonitrile, nitromethane, nitrobenzene, decalin, tetrahydrofuran, methyl cyclopentyl ether, dioxane and methyl tert-butyl ether;
the weakening agent of the Lewis acid in the step 1 is one or a mixture of more of tetramethylammonium chloride, tetraethylammonium chloride, tetramethylammonium bromide, tetraethylammonium bromide, lithium fluoride, potassium fluoride, sodium fluoride, lithium chloride, sodium chloride, potassium chloride, lithium bromide, sodium bromide and potassium bromide;
the Lewis acid in the step 1 is one or a mixture of more of aluminum trichloride, ferric trichloride, zinc chloride, boron trifluoride diethyl etherate, trifluoroacetic acid, methanesulfonic acid, trifluoromethanesulfonic acid, sulfuric acid and phosphoric acid;
the reaction temperature in the step 1 is between 0 and 150 ℃; the reaction time is 0.5 to 5 hours;
step 2, adding a certain amount of organosilane into the reaction liquid under stirring, and then adjusting the temperature of the reaction liquid to a preset range; then adding a certain amount of cyclohexanol compounds containing substituent groups, and carrying out heat preservation reaction for a preset time to obtain a product mainly containing a trans-substituted cyclohexyl compound;
2, the organosilane is one or more of trimethylsilane, triethylsilane, triisopropylsilane, tri-tert-butylsilane and trichlorosilane;
the organosilane in the step 2 is used in an equivalent ratio (the amount of the substance) of 110-300% of the cyclohexanol compound containing the substituent; when the cyclohexanol compound containing the substituent contains 2 or more than 2 hydroxyl groups which need to participate in the reaction, the usage of organosilane is increased in equal proportion;
the configuration of the cyclohexyl of the cyclohexanol compound containing the substituent in the step 2 is trans, cis or a cis-trans mixture;
the reaction temperature in the step 2 is-20 to 50 ℃; the reaction time is 1 to 30 hours;
the dosage of the solvent in the step 1 is 100-1000% of the mass ratio of the cyclohexanol compound containing the substituent in the step 2;
the dosage of the Lewis acid in the step 1 is 33 to 200 percent of equivalent (amount of substance) ratio of the cyclohexanol compound containing the substituent in the step 2; the dosage of the weakening agent of the Lewis acid is 2-200 percent of equivalent (amount of substance) ratio of the Lewis acid; the dosage of the Lewis acid and the weakening agent of the Lewis acid is increased in equal proportion when the cyclohexanol compound containing the substituent group in the step 2 contains 2 or more hydroxyl groups needing to participate in the reaction;
the general formula of the reaction equation is as follows:
A method for synthesizing a compound containing trans-substituted cyclohexyl is characterized by comprising the following steps: the obtained product is a mixture mainly containing a trans-substituted cyclohexyl compound, and the common chemical post-treatment and purification procedures are adopted to obtain the trans-substituted cyclohexyl compound with the purity of more than or equal to 99 percent; the common chemical post-treatment and purification process comprises one or more of hydrolysis, liquid separation, extraction, concentration, distillation or reduced pressure distillation, crystallization and recrystallization, filtration and column chromatography.
The invention uses cyclohexanol compound with substituent as raw material to react with organic silane and weakened Lewis acid, to obtain trans-substituted cyclohexyl compound with high selectivity.
Reducing hydroxyl of a secondary alcohol or tertiary alcohol compound into a hydrogen atom by using organic silane and Lewis acid; this is a classical organic synthesis method that has been widely used. The method is very similar to the method when used for treating the cyclohexanol compound (belonging to secondary alcohol or tertiary alcohol) containing substituent groups; meanwhile, the method has certain defects that Lewis acid can cause the substituted cyclohexyl compound to generate carbon cations, and side reactions of rearrangement and isomerization occur, so that the carbon cations are finally changed into various isomerization impurities which are difficult to purify and remove, and further the yield of the subsequent product purification process is reduced and the cost is increased; even when the process conditions such as the properties of the raw materials and the degree of fluctuation of the reaction temperature are unstable, most of the raw materials and the target product are changed into the isomerized impurities in the normal reaction time.
Compared with the similar method, the improvement of the invention is that: lewis acid is weakened, or the Lewis acid and a weakening agent are added to replace the Lewis acid; thereby reducing the rate (and proportion) of the side reactions of generating carbocation and carrying out rearrangement and isomerization on the raw materials or products; the conversion rate of the target product is improved from 70-85% to 85-97%; the conversion rate of isomerization impurities which are difficult to remove is reduced from 8-80 percent to 2-5 percent; ensures that the proportion of the raw materials and the target product which become the isomerization impurities does not exceed 5 percent in the preset reaction time even if the raw materials have different properties, the reaction temperature fluctuation degree is slightly larger, and the like.
Detailed Description
The following examples illustrate the invention in detail: the embodiment is implemented on the premise of the technical scheme of the invention, and a detailed implementation mode and a specific operation process are given. 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.
The invention discloses a method for synthesizing a compound containing trans-substituted cyclohexyl, which comprises the following specific implementation modes:
examples 1 to 2: the starting materials and the target products used are shown in the following reaction equation:
example 1:
100g of petroleum ether and 15.2g (0.07 mol) of tetraethylammonium tetrafluoroborate were added to a 500ml three-neck glass bottle under nitrogen. While stirring, 7.8g (0.105 mol) of trimethylsilane were added. Controlling the temperature to 40-50 ℃ under stirring, and then adding 10.0g (0.035 mol) of compound A1-1; after the addition, the temperature is kept between 40 ℃ and 50 ℃ and the stirring is continued for 1 hour. The reaction solution was poured into water for hydrolysis, followed by liquid separation and washing of the organic layer for 2 times, and then sampling was performed for gas chromatography analysis, with the results that 1.3% of the raw material A1-1 remained, 91.2% of the target product A1-2, 5.2% of the by-product A1-3, and 2.2% of the total content of the isomerized impurities. The organic layer was directly frozen, crystallized, filtered to give 8.1g of the target product A1-2, gas phase purity 98.8%, yield 85.7%.
Example 2:
100g of decalin and 1.01g (0.024 mol) of anhydrous lithium chloride were added to a 500ml three-neck glass flask under nitrogen. Heating to 130 to 150 ℃, adding 1.6g (0.012 mol) of powdery aluminum trichloride in batches, continuing stirring for 5 hours at 130 to 150 ℃, and then cooling to the temperature close to room temperature under the protection of nitrogen. Under stirring, 7.8g (0.105 mol) of trimethylsilane was added, then the temperature was controlled to 0-10 ℃ and 10.0g (0.035 mol) of Compound A1-1 was added; keeping the temperature at 0-10 ℃ after the addition, continuing stirring, respectively taking a small amount of reaction solution samples after keeping the temperature for 5 hours and 10 hours, hydrolyzing, separating the solution, washing an organic layer for 2 times, and then carrying out gas chromatography analysis. The results were: after the heat preservation is carried out for 5 hours, 0.7 percent of the raw material A1-1, 93.3 percent of the content of the target product A1-2, 5.8 percent of the content of the by-product A1-3 and 0.2 percent of the total content of the isomerization impurities remain. After the heat preservation is carried out for 10 hours, 0.2 percent of the raw material A1-1, 97.7 percent of the target product A1-2, 1.7 percent of the by-product A1-3 and 0.4 percent of the total content of the isomerization impurities are remained.
Comparative example 1:
100g of petroleum ether and 1.6g (0.012 mol) of flake aluminum trichloride were charged into a 500ml three-necked glass bottle under a nitrogen atmosphere. While stirring, 7.8g (0.105 mol) of trimethylsilane was added, then the temperature was controlled to 0-10 ℃ and 10.0g (0.035 mol) of Compound A1-1 was added; keeping the temperature at 0-10 ℃ after the addition, continuing stirring, respectively taking a small amount of reaction solution samples after keeping the temperature for 1 hour and 3 hours, hydrolyzing, separating the solution, washing an organic layer for 2 times, and then carrying out gas chromatography analysis. The results were: after the heat preservation is carried out for 1 hour, 0.7 percent of the raw material A1-1, 82.7 percent of the content of the target product A1-2, 12.1 percent of the content of the by-product A1-3 and 5.2 percent of the total content of the isomerization impurities remain. After the heat preservation is carried out for 3 hours, the raw material A1-1 is not detected, the content of the target product A1-2 is 63.5 percent, the content of the by-product A1-3 is 9.8 percent, and the total content of the isomerization impurities is 26.7 percent.
Comparative example 2:
100g of petroleum ether and 1.6g (0.012 mol) of powdery aluminum trichloride were charged into a 500ml three-necked glass bottle under a nitrogen atmosphere. Under stirring, 7.8g (0.105 mol) of trimethylsilane was added, then the temperature was controlled to 0-10 ℃ and 10.0g (0.035 mol) of Compound A1-1 was added; keeping the temperature at 0-10 ℃ after the addition, continuing stirring, respectively taking a small amount of reaction solution samples after 1 hour and 3 hours of heat preservation, hydrolyzing, then separating liquid, washing an organic layer for 2 times, and carrying out gas chromatography analysis. The results were: after the heat preservation is carried out for 1 hour, the raw material A1-1 cannot be detected, the content of the target product A1-2 is 50.1%, the content of the by-product A1-3 is 7.3%, and the total content of the isomerization impurities is 42.6%. After the heat preservation is carried out for 3 hours, the raw material A1-1 is not detected, the content of the target product A1-2 is 17.6 percent, the content of the by-product A1-3 is 2.7 percent, and the total content of the isomerization impurities is 79.7 percent.
Examples 3 to 4: the raw materials and the target product are shown in the following reaction equation:
example 3:
100g of methylene chloride and 39.6g (0.132 mol) of tetraethylammonium tetrachloroaluminate are placed in a 500ml three-neck glass bottle under nitrogen. While stirring, 50.7g (0.437 mol) of triethylsilane were added. Controlling the temperature to minus 20 to minus 10 ℃ under stirring, and then adding 100.0g (0.397 mol) of the compound A2-1; after the addition, the temperature is kept at minus 20 to minus 10 ℃ and the stirring is continued for 30 hours. Pouring the reaction solution into water for hydrolysis, then separating the solution, washing the organic layer for 2 times, sampling and carrying out gas chromatography analysis, wherein the results comprise 0.7% of the residual raw material A2-1, 90.7% of the target product A2-2, 7.2% of the byproduct A2-3 and 1.4% of the total content of the isomerized impurities.
Example 4:
200g of toluene and 0.413g (0.016 mol) of anhydrous lithium fluoride are introduced into a 500ml three-neck glass bottle under nitrogen protection. The temperature is reduced to 0 to 10 ℃, and boron trifluoride ether solution is added in portions, wherein the total content of boron trifluoride is 54.0g (0.794 mol). After the addition, the mixture was kept at 0 to 10 ℃ and stirred for 0.5 hour, then heated to a temperature close to room temperature, and 115.0g (0.99 mol) of triethylsilane was added. Controlling the temperature to be 0 to 10 ℃ under stirring, and then adding 100.0g (0.397 mol) of the compound A2-1; after the addition, the temperature is kept between 0 and 10 ℃ and stirring is continued for 10 hours. The reaction solution was poured into water for hydrolysis, followed by liquid separation and washing of the organic layer for 2 times, and then sampling was performed for gas chromatography analysis, with the results that 1.2% of the raw material A2-1 remained, 87.1% of the target product A2-2, 9.6% of the by-product A2-3, and 2.1% of the total content of the isomerized impurities.
Claims (1)
1. A method for synthesizing a compound containing trans-substituted cyclohexyl is characterized by comprising the following steps: the starting materials and the target products are shown in the following reaction equation:
heating to 130 to 150 ℃, adding 1.6g (0.012 mol) of powdery aluminum trichloride in batches, continuing stirring for 5 hours at the temperature of 130 to 150 ℃, and then cooling to the temperature close to room temperature under the protection of nitrogen;
under stirring, 7.8g (0.105 mol) of trimethylsilane was added, then the temperature was controlled to 0-10 ℃ and 10.0g (0.035 mol) of Compound A1-1 was added; keeping the temperature at 0-10 ℃ after the addition, continuing stirring, respectively taking a small amount of reaction solution samples after keeping the temperature for 5 hours and 10 hours, hydrolyzing, then separating the solution, washing an organic layer for 2 times, and carrying out gas chromatography analysis;
the results were: after the heat preservation is carried out for 5 hours, 0.7 percent of the raw material A1-1, 93.3 percent of the target product A1-2, 5.8 percent of the by-product A1-3 and 0.2 percent of the total content of the isomerization impurities are remained;
after the heat preservation is carried out for 10 hours, 0.2 percent of the raw material A1-1, 97.7 percent of the target product A1-2, 1.7 percent of the by-product A1-3 and 0.4 percent of the total content of the isomerization impurities remain.
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| AR047666A1 (en) * | 2004-02-20 | 2006-02-01 | Merck Sharp & Dohme | ESTEREOSELECTIVE SYNTHESIS OF CYCLOHEXANOPROPANOIC ACID 4,4-DISUBSTITUTED |
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