CN118026836A - Preparation method of 4-tert-butylcyclohexyl acetic acid or ester thereof - Google Patents

Preparation method of 4-tert-butylcyclohexyl acetic acid or ester thereof Download PDF

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CN118026836A
CN118026836A CN202410175700.8A CN202410175700A CN118026836A CN 118026836 A CN118026836 A CN 118026836A CN 202410175700 A CN202410175700 A CN 202410175700A CN 118026836 A CN118026836 A CN 118026836A
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黄汉民
丁永正
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University of Science and Technology of China USTC
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Abstract

The invention discloses a preparation method of 4-tert-butylcyclohexyl acetic acid or ester thereof, belonging to the technical field of organic chemistry. The preparation method of the 4-tert-butylcyclohexyl acetic acid or the ester thereof comprises the following steps: 1) Under the action of a metal catalyst, a phosphine ligand, an additive and an oxidant, water or alcohol and 4-tertiary butyl toluene are subjected to carbonylation reaction to prepare 4-tertiary butyl phenylacetic acid or ester thereof; 2) And (3) carrying out catalytic hydrogenation reaction on the 4-tert-butyl phenylacetic acid or the ester thereof obtained in the step (1) to obtain the 4-tert-butyl cyclohexyl acetic acid or the ester thereof. The preparation method is characterized in that the 4-tert-butylcyclohexyl acetic acid or the ester thereof is synthesized by a two-step method of carbonylation reaction and catalytic hydrogenation reaction, the reaction raw materials are easy to obtain, the reaction steps are simple and efficient, and the products are easy to separate, and compared with the traditional preparation method of the 4-tert-butylcyclohexyl acetic acid or the ester thereof, the preparation method has the advantages of low cost and high efficiency.

Description

Preparation method of 4-tert-butylcyclohexyl acetic acid or ester thereof
Technical Field
The invention relates to the technical field of organic chemistry, in particular to a preparation method of 4-tert-butylcyclohexyl acetic acid or ester thereof.
Background
Taylor disease is a blood protozoal disease that is a serious hazard to cattle. Buparvaquone is an effective drug for treating bovine theileriosis at present, and the domestic buparvaquone bulk drug at present mainly takes import. 4-tert-butylcyclohexyl acetic acid is one of the most main raw materials for synthesizing buparvaquone, and has important influence on the production cost and scale of the buparvaquone. At present, 4-tert-butylcyclohexyl acetic acid is mainly synthesized by the following three methods:
Scheme 1 (CN 105418363 a): the method uses the expensive 4-tertiary butyl cyclohexanone as the initial raw material, the target product can be obtained through three steps of reactions, and a large amount of phosphorus-containing wastewater can be generated, so that the method has the advantages of high environmental protection pressure and high cost. In addition, the product obtained by the method contains a trace amount of chloride ions, and the chloride ions are very easy to deactivate the catalyst in the subsequent step of synthesizing the buparvaquone, so that the method has strict requirements on the purity of the product.
Scheme 2 (j.am.chem.soc.1970, 92,2800): the method uses p-tert-butylbenzoic acid as a starting material, and the target product can be obtained through five steps of reactions, so that the reaction route is long. The product also contains a trace amount of chloride ions, which can affect the synthesis of buparvaquone.
Scheme 3 (can.j. Chem.1987,65,1859): the method also uses the relatively expensive p-tert-butylcyclohexanone as the initial raw material, the target product can be obtained through six steps of reactions, various wastes including toxic tin reagents can be generated in the reaction process, the environmental protection pressure is high, and the total yield is low.
Therefore, development of a simple and easily obtained compound which is used as a raw material, simple in steps and environment-friendly has important significance.
Disclosure of Invention
In view of the above, the present invention aims to provide a method for preparing 4-tert-butylcyclohexyl acetic acid or its ester. The preparation method has the advantages of readily available raw materials, simple synthesis steps, easy purification of products and low production cost.
In order to achieve the above purpose, the invention adopts the following technical scheme:
The invention provides a preparation method of 4-tert-butylcyclohexyl acetic acid or ester thereof, which comprises the following steps:
1) Under the action of a metal catalyst, a phosphine ligand, an additive and an oxidant, water or alcohol and 4-tertiary butyl toluene are subjected to carbonylation reaction to prepare 4-tertiary butyl phenylacetic acid or ester thereof;
2) And (3) carrying out catalytic hydrogenation reaction on the 4-tert-butyl phenylacetic acid or the ester thereof obtained in the step (1) to obtain the 4-tert-butyl cyclohexyl acetic acid or the ester thereof.
The invention synthesizes 4-tertiary butyl cyclohexyl acetic acid or ester thereof by a two-step method of carbonylation reaction and catalytic hydrogenation reaction.
The reaction equation is as follows:
The preparation method has the advantages of simple flow, easily obtained raw materials and higher product yield. Preferably, the metal catalyst in the step 1) is selected from one or more of cobalt-based catalyst, nickel-based catalyst and copper-based catalyst.
Preferably, the cobalt-based catalyst is selected from one or more of cobaltocene octacarbonyl, cobalt chloride, cobalt bromide, cobalt acetylacetonate and cobalt nitrate.
Preferably, the nickel-based catalyst is selected from one or more of nickel chloride, nickel bromide, nickel iodide, nickel acetate, nickel sulfate, nickel acetylacetonate and nickel nitrate; more preferably one or more of nickel chloride, nickel bromide, nickel iodide. In some embodiments of the invention, nickel iodide is preferred.
Preferably, the copper-based catalyst is selected from one or more of copper chloride, cuprous chloride, cupric bromide, cuprous iodide, cupric acetate and cupric acetylacetonate.
Preferably, the phosphine ligand in the step 1) is selected from one or more of N-butyl di (1-adamantyl) phosphine, benzyl di adamantyl phosphine, 2-dicyclohexylphosphino-2 ' - (N, N-dimethylamino) biphenyl, 2-dicyclo hexylphosphine-2 ',6' -diisopropyloxybiphenyl, 2-dicyclohexylphosphine-2 ',6' -dimethoxy biphenyl and diphenyl phosphine oxide; more preferably one or more of N-butyl bis (1-adamantyl) phosphine, benzyl bis adamantyl phosphine, 2-dicyclohexylphosphino-2' - (N, N-dimethylamino) biphenyl. In some embodiments of the invention, n-butyl bis (1-adamantyl) phosphine is preferred. In the invention, the additive can promote the miscibility of water and organic phase, and improve the reaction yield.
Preferably, the additive is selected from one or more of quaternary ammonium salt, crown ether and chain polyether.
The quaternary ammonium salts include, but are not limited to, tetrabutylammonium bromide or tetrabutylammonium iodide, and the like.
Such crown ethers include, but are not limited to, 18-crown-6 or 15-crown-5, and the like.
Such chain polyethers include, but are not limited to, polyethylene glycol dialkyl ethers and the like.
In some embodiments of the invention, the additive is selected from tetrabutylammonium iodide.
In the present invention, the oxidizing agent may be used as an activating agent to convert 4-t-butyltoluene into radicals.
Preferably, the oxidizing agent is selected from peroxides or persulfates.
The peroxides include, but are not limited to, di-t-butyl peroxide, hydrogen peroxide, t-butyl peroxybenzoate, t-butyl peroxide, and the like.
The persulfate includes, but is not limited to, potassium persulfate, sodium persulfate, and the like.
In some embodiments of the invention, the oxidizing agent is preferably di-t-butyl peroxide.
The 4-tertiary butyl toluene in the carbonylation reaction in the step 1) can be used as a reaction raw material and a reaction solvent.
After completion of step 1) of the above preparation method, 4-tert-butyltoluene may be recovered by distillation.
Preferably, the catalyst for catalyzing the hydrogenation reaction in the step 2) is selected from ruthenium carbon or ruthenium and aluminum oxide composite catalysts.
The solvent for the catalytic hydrogenation reaction in step 2) is selected from alcohol solvents.
The alcohol solvent is preferably one or more of methanol, ethanol and isopropanol.
In some embodiments of the present invention, specifically:
1) Under the action of nickel iodide, n-butyl di (1-adamantyl) phosphine, tetrabutylammonium iodide and di-tert-butyl peroxide, 4-tert-butyltoluene is taken as a raw material, and is subjected to carbonylation reaction with carbon monoxide and water to prepare 4-tert-butylphenylacetic acid;
2) And (3) carrying out catalytic hydrogenation reaction on the 4-tert-butyl phenylacetic acid obtained in the step (1) under the action of ruthenium carbon to obtain the 4-tert-butyl cyclohexyl acetic acid.
Or in some embodiments of the invention, specifically:
1) Under the action of nickel iodide, n-butyl di (1-adamantyl) phosphine, tetrabutylammonium iodide and di-tert-butyl peroxide, 4-tert-butyltoluene is taken as a raw material, and is subjected to carbonylation reaction with carbon monoxide and ethanol to prepare 4-tert-butylphenylacetic acid ethyl ester;
2) And (3) carrying out catalytic hydrogenation reaction on the ethyl 4-tert-butyl phenylacetate obtained in the step (1) under the action of ruthenium carbon to obtain the ethyl 4-tert-butyl cyclohexyl acetate.
Preferably, the molar ratio of 4-tert-butyltoluene to carbon monoxide in the step 1) is (1-5): 1, a step of; more preferably 1.5:1.
The molar ratio of the water or the alcohol to the carbon monoxide is (0.1-0.5): 1, a step of; more preferably 0.25:1.
Preferably, the molar ratio of the metal catalyst to the oxidizing agent in the step 1) is (0.001 to 0.05): 1, a step of; more preferably 0.01:1.
Preferably, the molar ratio of phosphine ligand to oxidant in step 1) is (0.001-0.05): 1, a step of; more preferably 0.01:1.
Preferably, the molar ratio of the additive to the oxidant in the step 1) is (0.001 to 0.05): 1, a step of; more preferably 0.01:1.
Preferably, the molar ratio of the oxidant to the carbon monoxide in the step 1) is (0.05 to 1): 1, a step of; more preferably 0.125:1.
Preferably, the molar ratio of the catalyst for the catalytic hydrogenation reaction in the step 2) to 4-tert-butylphenylacetic acid or an ester thereof is (0.01 to 0.15): 1, a step of; more preferably 0.1:1.
Preferably, the molar ratio of the hydrogen gas of the catalytic hydrogenation reaction in the step 2) to the 4-tert-butylphenylacetic acid or the ester thereof is (5 to 30): 1. more preferably 20:1.
Preferably, the temperature of the carbonylation reaction in the step 1) is 60-180 ℃; more preferably from 90℃to 150 ℃. In some embodiments of the invention, 120℃is preferred.
Preferably, the pressure of carbon monoxide in the step 1) is 1 to 60atm; more preferably 30 to 50atm; further preferably 40atm.
Preferably, the temperature of the catalytic hydrogenation reaction in the step 2) is between room temperature and 160 ℃; more preferably 80 ℃.
The room temperature is preferably 10 to 30 ℃.
Preferably, the hydrogen pressure of the catalytic hydrogenation reaction in the step 2) is 10 to 60atm; more preferably 20 to 40atm. In some embodiments of the present invention, 30atm is preferred.
The preparation method has the advantages of few reaction byproducts, large difference between the byproducts and the product properties, convenience in separation and post-treatment and high product purity.
The invention also provides application of the preparation method in the synthesis of buparvaquone.
Compared with the prior art, the preparation method of the 4-tert-butylcyclohexyl acetic acid or the ester thereof provided by the invention comprises the following steps: 1) Under the action of a metal catalyst, a phosphine ligand, an additive and an oxidant, water or alcohol and 4-tertiary butyl toluene are subjected to carbonylation reaction to prepare 4-tertiary butyl phenylacetic acid or ester thereof; 2) And (3) carrying out catalytic hydrogenation reaction on the 4-tert-butyl phenylacetic acid or the ester thereof obtained in the step (1) to obtain the 4-tert-butyl cyclohexyl acetic acid or the ester thereof. The preparation method is characterized in that the 4-tert-butylcyclohexyl acetic acid or the ester thereof is synthesized by a two-step method of carbonylation reaction and catalytic hydrogenation reaction, the reaction raw materials are easy to obtain, the reaction steps are simple and efficient, and the products are easy to separate, and compared with the traditional preparation method of the 4-tert-butylcyclohexyl acetic acid or the ester thereof, the preparation method has the advantages of low cost and high efficiency.
Detailed Description
In order to further illustrate the present invention, the following describes in detail the preparation method of 4-t-butylcyclohexylacetic acid or an ester thereof according to the present invention with reference to examples.
The chemical reagents used in the examples below were all common commercial products.
The volume of the reaction vessels used in the examples below was 300mL.
Example 1
Step 1: synthesis of 4-tert-butylphenylacetic acid
Nickel iodide (156.3 mg), n-butylbis (1-adamantyl) phosphine (179.3 mg), tetrabutylammonium iodide (184.7 mg), 4-t-butyltoluene (100 mL), water (1.8 mL), and di-t-butyl peroxide (9.1 mL) were added to the reaction vessel, carbon monoxide was substituted 3 times, carbon monoxide at 30atm was charged, and the reaction was stirred at 140℃for 12 hours. After the completion of the reaction, the system was cooled to room temperature, and then carbon monoxide was removed, by-products were removed by distillation under reduced pressure, and 4-t-butyltoluene was recovered. The residue was washed with water and extracted with ethyl acetate, dried, concentrated and recrystallized to give 7.1g of a white solid in yield 74％.1H NMR(400MHz,CDCl3):δ7.39(d,J＝8.3Hz,2H),7.25(d,J＝8.2Hz,2H),3.65(s,2H),1.34(s,9H).13C NMR(100MHz,CDCl3):δ178.1,150.1,130.3,129.0,125.6,40.6,34.5,31.2.
Step2: synthesis of 4-tert-butylcyclohexyl acetic acid
3.8G of 4-t-butylphenylacetic acid, 30mL of ethanol and 380mg of ruthenium carbon were charged into the reaction vessel, and then replaced 3 times with nitrogen and 2 times with hydrogen. After the replacement, 30atm of hydrogen was charged into the autoclave and stirred at 80℃until the pressure in the autoclave stabilized. After the reaction, the system was cooled to room temperature and hydrogen was evolved. The system was then filtered to remove the catalyst and the filtrate was concentrated to 10mL. The concentrate was then slowly poured into 30mL of water and stirred for 10min, a large amount of white solid precipitated. Filtering, drying the obtained solid to obtain white solid 3.8g, yield 96％.1H NMR(400MHz,CDCl3):δ9.72(s,1H),2.44(d,J＝8Hz,1H),2.25(d,J＝7Hz,1H),1.49-1.91(m,5H),0.89-1.18(m,5H),0.83-–0.85(m,9H).13C NMR(100MHz,CDCl3):δ179.2,178.6,48.3,47.6,41.7,36.1,34.9,33.4,32.5,32.4,30.5,29.6,29.3,27.6,27.5,26.9,26.3,21.6.
Example 2
Step 1: synthesis of ethyl 4-tert-butylphenylacetate
Nickel iodide (156.3 mg), n-butylbis (1-adamantyl) phosphine (179.3 mg), tetrabutylammonium iodide (184.7 mg), 4-t-butyltoluene (100 mL), ethanol (5.8 mL), and di-t-butyl peroxide (9.1 mL) were added to the reaction vessel, carbon monoxide was substituted 3 times, carbon monoxide at 30atm was charged, and the reaction was stirred at 140℃for 12 hours. After the completion of the reaction, the reaction system was cooled to room temperature, and then carbon monoxide was removed, 4-tert-butyltoluene was recovered by distillation under reduced pressure to give 8.9g of a product in a yield 81％.1H NMR(400MHz,CDCl3):δ7.37(d,J＝8.2Hz,2H),7.23(d,J＝8.2Hz,2H),4.15(q,J＝7.2Hz,2H),3.60(s,2H),1.33(s,9H),1.26(t,J＝7.1Hz,3H).13C NMR(100MHz,CDCl3):δ172.0,150.1,131.3,129.0,125.6,60.8,40.9,34.5,31.3,14.2.
Step 2: synthesis of ethyl 4-tert-butylcyclohexyl acetate
4.4G of ethyl 4-t-butylphenylacetate, 30mL of ethanol and 380mg of ruthenium carbon were charged into the reaction vessel, and then replaced with nitrogen 3 times and hydrogen 2 times. After the replacement, 30atm of hydrogen was charged into the autoclave and stirred at 80℃until the pressure in the autoclave stabilized. After the reaction, the system was cooled to room temperature and hydrogen was evolved. The system was then filtered to remove the catalyst and the filtrate was concentrated. Then the concentrated solution is distilled under reduced pressure to obtain 4.4g of product with yield 97％.1H NMR(400MHz,CDCl3):δ4.11-4.18(m,2H),2.38–-2.17(m,2H),1.89-1.48(m,5H),1.30-–1.26(m,3H),1.13-0.94(m,5H),0.85-–0.86(m,9H).13C NMR(100MHz,CDCl3):δ173.6,173.2,60.1,48.5,47.7,42.1,36.6,35.2,33.4,32.5,32.4,30.6,29.6,27.6,27.4,27.1,27.0,21.6,14.3.
The above description of the embodiments is only for aiding in the understanding of the method of the present invention and its core ideas. It should be noted that it will be apparent to those skilled in the art that various modifications and adaptations of the invention can be made without departing from the principles of the invention and these modifications and adaptations are intended to be within the scope of the invention as defined in the following claims.

Claims (10)

1. A process for the preparation of 4-tert-butylcyclohexylacetic acid or an ester thereof, comprising the steps of:
1) Under the action of a metal catalyst, a phosphine ligand, an additive and an oxidant, water or alcohol and 4-tertiary butyl toluene are subjected to carbonylation reaction to prepare 4-tertiary butyl phenylacetic acid or ester thereof;
2) And (3) carrying out catalytic hydrogenation reaction on the 4-tert-butyl phenylacetic acid or the ester thereof obtained in the step (1) to obtain the 4-tert-butyl cyclohexyl acetic acid or the ester thereof.
2. The method according to claim 1, wherein the metal catalyst in step 1) is one or more selected from the group consisting of cobalt-based catalyst, nickel-based catalyst, and copper-based catalyst.
3. The preparation method according to claim 2, wherein the cobalt-based catalyst is selected from one or more of cobalt octacarbonyl, cobalt chloride, cobalt bromide, cobalt acetylacetonate, and cobalt nitrate;
The nickel-based catalyst is selected from one or more of nickel chloride, nickel bromide, nickel iodide, nickel acetate, nickel sulfate, nickel acetylacetonate and nickel nitrate;
The copper-based catalyst is selected from one or more of copper chloride, cuprous chloride, cupric bromide, cuprous iodide, cupric acetate and cupric acetylacetonate.
4. The preparation method according to claim 1, wherein the phosphine ligand in the step 1) is selected from one or more of N-butyl bis (1-adamantyl) phosphine, benzyl diamantane, 2-dicyclohexylphosphino-2 ' - (N, N-dimethylamino) biphenyl, 2-dicyclohexylphosphine-2 ',6' -diisopropyloxybiphenyl, 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl, and diphenylphosphino.
5. The preparation method according to claim 1, wherein the additive is one or more selected from the group consisting of quaternary ammonium salts, crown ethers and chain polyethers.
6. The method of claim 1, wherein the oxidizing agent is selected from the group consisting of peroxides and persulfates.
7. The process according to claim 1, wherein the catalyst for the catalytic hydrogenation reaction in step 2) is selected from ruthenium carbon or ruthenium and alumina composite catalysts.
8. The process according to claim 1, wherein the molar ratio of 4-t-butyltoluene to carbon monoxide in step 1) is (1 to 5): 1, a step of;
The molar ratio of water or alcohol to carbon monoxide in the step 1) is (0.1-0.5): 1, a step of;
the molar ratio of the metal catalyst to the oxidant in the step 1) is (0.001 to 0.05): 1, a step of;
the molar ratio of phosphine ligand to oxidant in step 1) is (0.001-0.05): 1, a step of;
The molar ratio of the additive to the oxidant in the step 1) is (0.001-0.05): 1, a step of;
The molar ratio of the oxidant to the carbon monoxide in the step 1) is (0.05-1): 1, a step of;
The molar ratio of the catalyst for the catalytic hydrogenation reaction in the step 2) to 4-tert-butylphenylacetic acid or the ester thereof is (0.01 to 0.15): 1, a step of;
The molar ratio of the hydrogen for the catalytic hydrogenation reaction in the step 2) to the 4-tert-butylphenylacetic acid or the ester thereof is (5-30): 1.
9. The process according to claim 1, wherein the carbonylation reaction in step 1) is carried out at a temperature of 60 ℃ to 180 ℃;
the pressure of carbon monoxide in the step 1) is 1 to 60atm;
The temperature of the catalytic hydrogenation reaction in the step 2) is between room temperature and 160 ℃;
the hydrogen pressure of the catalytic hydrogenation reaction in the step 2) is 10 to 60atm.
10. Use of the preparation method according to any one of claims 1 to 9 for the synthesis of buparvaquone.
CN202410175700.8A 2024-02-06 2024-02-06 Preparation method of 4-tert-butylcyclohexyl acetic acid or ester thereof Pending CN118026836A (en)

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