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Preparing method of compound with trans-1,4-cyclohexylidene structure

A manufacturing method and compound technology, applied in organic isomerization, chemical instruments and methods, organic chemistry, etc., can solve the problems of low selectivity between cis-isomers and trans-isomers, difficulty in obtaining trans-isomers, and inability to manufacture

Active Publication Date: 2011-05-18
DIC CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Regarding these methods, although any of them uses an alcoholic solvent such as ethanol as a reaction solvent, in these reactions, when a compound having an oxygen atom in a substituent having substrate selectivity is used as a raw material, the The ratio of the trans-isomer of the obtained compound increases
Therefore, it is not a method applicable to all compounds. For a compound such as an alkylcyclohexane, the atoms directly bonded to the cyclohexane skeleton are only carbon atoms and hydrogen atoms. Cannot be produced by stereoselective reduction
In addition, in the conventional stereoselective reduction, the selectivity of the cis-isomer and the trans-isomer is low, and the production ratios of the trans-isomer are 72% and 68%, respectively, which is insufficient.
As mentioned above, it is difficult to selectively obtain the trans isomer by catalytic reduction of cyclohexene derivatives having unsaturated bonds in the cyclohexane structure

Method used

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  • Preparing method of compound with trans-1,4-cyclohexylidene structure
  • Preparing method of compound with trans-1,4-cyclohexylidene structure
  • Preparing method of compound with trans-1,4-cyclohexylidene structure

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] (Example 1) trans, trans-4-ethyl-4'-propyl bicyclohexane production

[0056] 【Reaction 1】

[0057]

[0058] Add 400 g of ethyl triphenylphosphonium bromide, 200 g of 4-(trans-4'-propylcyclohexyl) cyclohexanone and tetrahydrofuran (THF) into a 2L 4-neck flask (with a mechanical stirrer and a thermometer). 500mL, ice-cooled. A THF solution (360 mL) of 122 g of potassium tert-butoxide was added dropwise thereto over 30 minutes, followed by stirring at 10° C. for 2 hours. Water was added, and after stirring, the organic layer was separated, and the aqueous layer was extracted with hexane. The organic layers were combined, washed with water, 50% methanol aqueous solution, and saturated brine, and the solvent was distilled off under reduced pressure, followed by purification to obtain 186 g of trans-4-ethylidene-4'-propylbicyclohexane.

[0059] 1 H-NMR (400MHz, CDCl 3 ): 0.85-1.15(m, 17H), 1.27-1.31(m, 3H), 1.54-1.76(m, 6H), 1.94-2.01(m, 1H), 2.15-2.21(m, 1H), 2.59-2....

Embodiment 2

[0065]In Example 1, the reaction solvent of the hydrogenation reaction was changed to tetrahydrofuran (THF), except that, the same operation was performed, and trans, trans-4-ethyl-4'-propylbicyclohexyl Production of alkanes. As in Example 1, the isomer ratio was measured by GC, and the trans, cis isomer was 15%, and the trans, trans isomer was 85%. Through the production method of the present invention, the trans-form and trans-isomers can be obtained with a high purity of 85%.

Embodiment 3

[0067] In Example 1, except that the reaction solvent of the hydrogenation reaction was changed to acetone, trans,trans-4-ethyl-4'-propylbicyclohexane was produced in the same manner. . As in Example 1, the isomer ratio was measured by GC, and the trans, cis isomer was 15%, and the trans, trans isomer was 85%. Through the production method of the present invention, the trans-form and trans-isomers can be obtained with a high purity of 85%.

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Abstract

The invention provides a preparing method of a high-efficiency compound provided with a trans-1,4-cyclohexylidene structure and using as a raw material of medicines, pesticides and liquid crystal materials, etc. By performing catalytic hydrogenation on alkyl methylene cyclohexane derivatives with aprotic solvents of ethyl acetate, acetone and tetrahydrofuran as the reaction solvent, the compound with a trans-1,4-alkyl cyclohexylidene structure can be highly selectively obtained. By making alkyl phosphorus ylide or phosphonate derivatives acting on cyclohexanone derivatives, the alkyl methylene cyclohexane derivatives can be obtained in an alkaline condition.

Description

technical field [0001] The present invention relates to the manufacture of compounds having a trans-1,4-cyclohexylene structure. Background technique [0002] Compounds having a trans-cyclohexylene structure are often used as raw materials for pharmaceuticals, agricultural chemicals, liquid crystal materials, and the like. Although cyclohexane has cis-isomers and trans-isomers, among them, the trans-isomers are often useful in terms of physical properties. [0003] Conventionally, studies have been made on methods for selectively producing only the trans-isomer, but there is no method for obtaining a compound having a trans-cyclohexylene structure in a short process and in high yield. In terms of its production method, it is mainly divided into the following two methods: after obtaining a mixture of cis-isomer and trans-isomer, the mixture with excess trans-isomer is produced through isomerization reaction, and the trans-isomer is obtained by purification. and, by using a ...

Claims

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Application Information

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IPC IPC(8): C07B37/08C07B37/02C07C13/28C07C5/13
Inventor 楠本哲生大泽政志门本丰
Owner DIC CORP
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