Synthetic method for 4-tertiary butyl cyclohexaneacetic acid

A technology for the synthesis of tert-butylcyclohexanone and its method is applied in the field of synthesis of chemical drug intermediates, achieving the effects of high yield, low price and simple post-treatment

Inactive Publication Date: 2016-03-23
山东川成医药有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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  • Synthetic method for 4-tertiary butyl cyclohexaneacetic acid
  • Synthetic method for 4-tertiary butyl cyclohexaneacetic acid

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Embodiment 1

[0025] The synthetic method of 4-tert-butylcyclohexylacetic acid, step is as follows:

[0026] Step 1, Synthesis of ethyl 4-tert-butylcyclohexaneylidene acetate

[0027] Suspend 14.74g (0.37mol) of sodium hydride (commercially available content 60%) in 500mL dry tetrahydrofuran, stir and cool the reaction system to 0°C with a cold trap, drop 76.6mL (0.386mol) of triethyl phosphoroacetate Add to the above reaction system and stir at 0°C for 15 minutes, dissolve 54g (0.35mol) of 4-tert-butylcyclohexanone in 100mL tetrahydrofuran, add dropwise to the above reaction system at 0°C, after the addition is complete The temperature of the reaction system was raised to room temperature, and the reaction was stirred at room temperature for another 2 hours, then the reaction was quenched with 500 mL of water, concentrated under reduced pressure to remove part of tetrahydrofuran, and then the aqueous phase was extracted with 300 mL×2 methyl tert-butyl ether, and the organic phase was Comb...

Embodiment 2

[0033] Embodiment 2: comparative example

[0034] 1) Synthesis of ethyl 4-tert-butylcyclohexaneylidene acetate (adjust the molar ratio of 4-tert-butylcyclohexanone to triethyl phosphoroacetate to 1:1.3)

[0035] Suspend 14.74g (0.37mol) of sodium hydride (commercially available content 60%) in 500mL dry tetrahydrofuran, stir and cool the reaction system to 0°C with a cold trap, drop 76.6mL (0.386mol) of triethyl phosphoroacetate Add it to the above reaction system and stir at 0°C for 15 minutes, dissolve 45.7g (0.296mol) of 4-tert-butylcyclohexanone in 100mL tetrahydrofuran, add it dropwise to the above reaction system at 0°C, and the addition is complete Afterwards, the temperature of the reaction system was raised to room temperature, and the reaction was stirred at room temperature for another 2 hours, then the reaction was quenched with 500ml of water, concentrated under reduced pressure to remove part of tetrahydrofuran, and then the aqueous phase was extracted with 300mL...

Embodiment 3

[0040] Embodiment 3: comparative example

[0041] Synthesis of ethyl 4-tert-butylcyclohexyl acetate (increase the hydrogen pressure to 3MPa during the hydrogenation reduction reaction)

[0042]Place 50 g (0.22 mol) of ethyl 4-tert-butylcyclohexaneylidene acetate and 500 mL of methanol in a 1L high-pressure hydrogenation reactor, add 2.9 g of Raney nickel, replace the hydrogenation tank with hydrogen for three times, and pressurize with hydrogen after removing the air To 3MPa, heat the system to 55°C to carry out the hydrogenation reduction reaction. The reaction is considered to be over when the pressure no longer drops. The whole reaction takes 3.5 hours (when the hydrogen pressure is lower than 2MPa during the reaction, replenish hydrogen in time to keep the reaction Hydrogen pressure is 3MPa). Then the pressure was released, the reaction system was filtered to remove Raney nickel, and the filtrate was concentrated to obtain 48.1 g of oily product, namely ethyl 4-tert-butyl...

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Abstract

The invention provides a synthetic method for 4-tertiary butyl cyclohexaneacetic acid. The synthetic method comprises the steps of: firstly adding sodium hydride into dried tetrahydrofuran; stirring the mixture and reducing the temperature to 0 DEG C; adding triethyl phosphonoacetate and stirring the mixture; adding a tetrahydrofuran solution of 4-tertiary butyl cyclohexanone, and raising the temperature to room temperature and stirring the mixture; then adding obtained 4-tertiary butyl ethyl cyclohexylideneacetate into methanol; then adding raney nickel to react in a hydrogen atmosphere; and finally mixing the 4-tertiary butyl ethyl cyclohexylacetate with an aqueous solution of sodium hydroxide, and heating and stirring the mixture to obtain the 4-tertiary butyl cyclohexaneacetic acid. The method provides the effective method for producing the 4-tertiary butyl cyclohexaneacetic acid. The method is few in step, high in yield, simple in post-treatment such as purification and easy for industrial production and operation.

Description

technical field [0001] The invention belongs to the technical field of synthesis of chemical drug intermediates, in particular to a method for synthesizing 4-tert-butylcyclohexylacetic acid, a drug bupavaquinone intermediate. Background technique [0002] Bupavaquinone (Formula I) is a drug developed by Pitman-Moore Company for the treatment of cattle theilesiosis, which is a blood protozoan disease that is seriously harmful to cattle, and the onset season is generally every year. From May to August, the mortality rate is 6% to 60%. Bupavaquone was listed in some countries in Africa, the Middle East and the Far East in 1991. It is currently the most effective drug for the treatment of cattle theilesisis. The treatment dose is 2.5 mg / kg, and the cure rate is about 90% to 98%. between. [0003] Formula I. [0004] So far, there are three methods for the synthesis of bupavaquinone reported in the literature: 1) Using 2-chloro-1,4-naphthoquinone and p-tert-butylcyclohexylac...

Claims

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Application Information

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IPC IPC(8): C07C27/02C07C53/134
CPCC07C51/09C07C67/303C07C67/343C07C53/134C07C69/608
Inventor 刘怀振马居良田延红沈乃涛郭明李文丽
Owner 山东川成医药有限公司
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