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The synthetic method of diphenylcyclohexylmethanol

A technology of cyclohexylmethanol and synthesis method, which is applied in the field of preparation of organic compound diphenylcyclohexylmethanol, can solve the problems of harsh reaction conditions, slow reaction speed, large amount of magnesium, etc., achieve convenient post-processing and avoid the use of catalysts , high purity and high yield

Inactive Publication Date: 2020-04-17
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The preparation of diphenylcyclohexylmethanol by Grignard reaction is slow, the reaction conditions are harsh, the yield is very low, the amount of magnesium is large, and solid waste is difficult to handle

Method used

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  • The synthetic method of diphenylcyclohexylmethanol

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] The synthetic method of embodiment 1, diphenylcyclohexylcarbinol, carries out following steps successively:

[0048] (1) Under the protection of an inert gas (nitrogen), add 23g (1mol) of sodium, 300mL of toluene, and 4mL of oleic acid into the reaction device, heat up to reflux (110°C) and stir, stop heating after reflux for 1h, and stir at high speed; Let cool to room temperature.

[0049] (2), under the protection of inert gas (nitrogen), slowly drop 56g (0.5mol) chlorobenzene and 50mL toluene mixed solution in step (1) gained liquid, the temperature of control reaction system is not more than 40 during the dropping process ℃; After the dropwise addition, react at 30℃ for 2h.

[0050](3), under the protection of inert gas (nitrogen), 47g (0.25mol) methyl cyclohexanecarboxylate is slowly added dropwise to the liquid obtained in step (2), and the dropping time is 30min; ℃ reaction 2h, that is, stop the reaction.

[0051] (4), the solution obtained in step (3) was le...

Embodiment 2

[0057] The synthetic method of embodiment 2, diphenylcyclohexylcarbinol, carries out following steps successively:

[0058] (1) Under the protection of an inert gas (nitrogen), add 23g (1mol) sodium, 300mL xylene, and 4g sodium stearate to the reaction device, heat up to reflux (137°C) and stir, and stop heating after reflux for 1h , stirring at high speed; until cooled to room temperature.

[0059] (2), under the protection of inert gas (nitrogen), slowly drop 63g (0.56mol) chlorobenzene and 60mL xylene mixed solution in step (1) gained liquid, the temperature of control reaction system is not more than 40°C; after the dropwise addition, react at 30°C for 2h.

[0060] (3), under the protection of inert gas (nitrogen), 47g (0.25mol) methyl cyclohexanecarboxylate is slowly added dropwise to the liquid obtained in step (2), and the dropping time is 30min; ℃ reaction 2h, that is, stop the reaction.

[0061] (4), the reaction liquid obtained in step (3) was left to stand, filte...

Embodiment 3

[0064] The synthetic method of embodiment 3, diphenylcyclohexylcarbinol, carries out following steps successively:

[0065] (1), under the protection of inert gas (nitrogen), add 23g (1mol) sodium, 300mL toluene, 4mL oleic acid to the reaction device, heat up to reflux and stir, stop heating after reflux for 1h, and stir at high speed; until cold to room temperature.

[0066] (2), under the protection of inert gas (nitrogen), slowly drop 78.5g (0.5mol) bromobenzene and 80mL toluene mixed solution in the liquid obtained in step (1), control the temperature of the reaction system in the dropping process not to exceed 40°C; after the dropwise addition, react at 30°C for 2h.

[0067] (3) Under the protection of an inert gas (nitrogen), slowly drop 38g (0.2mol) of methyl cyclohexanecarboxylate into the solution obtained in step (2) for 30 minutes; keep at 40°C after the addition is completed After 2 hours of reaction, the reaction was stopped.

[0068] (4), the reaction solution...

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Abstract

The invention discloses a synthesis method of diphenylcyclohexylcarbinol. The synthesis method sequentially comprises the following steps: adding higher fatty acid or higher fatty acid salt into an organic solvent under the protection of inert gas, adding sodium or granular sodium, dropwise adding halogenated benzene to react with a mixed solution of the organic solvent, then dropwise adding methyl cyclohexanecarboxylate to react, standing the obtained reaction liquid, filtering, and adding a hydrochloric acid solution or an ammonium chloride aqueous solution into the filtrate to carry out a hydrolysis reaction; statically separating the obtained reaction liquid, evaporating the organic solvent from an organic phase, performing rectification under vacuum to obtain a colorless transparent oily substance, and curing at room temperature to obtain the diphenylcyclohexylcarbinol. The method for preparing the diphenylcyclohexylcarbinol has the technical advantages of high efficiency, economy, greenness and suitability for industrialized production requirements and the like.

Description

technical field [0001] The present invention relates to the preparation method of organic compound diphenylcyclohexylmethanol. Background technique [0002] Diphenylcyclohexylcarbinol is an important fine chemical intermediate. Due to its large group steric hindrance, some chiral monomers containing this group can form a helical structure during polymerization and be used in polymers. material field. [0003] At present, there are few synthetic techniques related to diphenylcyclohexylcarbinol, and there are mainly two types: [0004] 1. Synthesis method of cyclohexyl phenyl ketone: (1) literature (Angewandte Chemie, 2011, 50, 45, 10703-10707) proposes to react cyclohexyl phenyl ketone and phenylboronic acid under the action of a metal catalyst to synthesize diphenyl Cyclohexylmethanol; (2) literature (Nature Communications, 2016,7,10337) proposes that cyclohexyl phenyl ketone and tetraphenylphosphine iodide are combined in Cs 2 CO 3 The synthesis of diphenylcyclohexylmet...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C29/09C07C33/34
CPCC07C29/09C07C29/68C07C2601/14C07C33/34
Inventor 陈新志毛崇智钱超
Owner ZHEJIANG UNIV
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