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Method for preparing allyl alcohol compounds from alpha,beta-unsaturated aldehyde ketones

An unsaturated compound technology, applied in the preparation of organic compounds, chemical instruments and methods, preparation of carboxylic acid nitrile, etc., can solve the problem of low catalyst activity, and achieve the effects of high product purity, mild preparation conditions and high economic value

Inactive Publication Date: 2015-09-30
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although some progress has been made in catalyzing the transfer hydrogenation of α, β-unsaturated aldehydes and ketones in aqueous phase, most of the water-soluble catalysts have relatively low activity, which can realize efficient and selective transfer hydrogenation of functional groups in aqueous phase. The system is rarely reported (Nieto I, Livings MS, Sacci III JB, et al.Organometallics.2011, 30(23):6339-6342, Aliende C, Pérez-Manrique M, Jalón FlA, et al.Organometallics.2012 ,31(17):6106-6123.)

Method used

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  • Method for preparing allyl alcohol compounds from alpha,beta-unsaturated aldehyde ketones
  • Method for preparing allyl alcohol compounds from alpha,beta-unsaturated aldehyde ketones
  • Method for preparing allyl alcohol compounds from alpha,beta-unsaturated aldehyde ketones

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Experimental program
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Effect test

Embodiment 1

[0019] Preparation of catalyst stock solution: Add 5.0 μmol of catalyst [Cp*Ir(6-OH-py-pz)(OH 2 )]SO 4 (IV) Add 2 mL of deionized water to prepare a solution with a concentration of 5 μmol / mL. The solution was evacuated / nitrogen replaced three times, then the round bottom flask was frozen in liquid nitrogen under a nitrogen blanket until the solution was completely frozen solid. Then, under vacuum conditions, the round bottom flask was slowly heated in warm water to remove dissolved oxygen and other gases in the aqueous solution. After the solid is completely dissolved, fill it with nitrogen, and perform "liquid nitrogen freezing and degassing-vacuumizing-nitrogen protection thawing" again, repeating three times. Finally, the catalyst solution was stored under nitrogen protection for future use.

[0020] Preparation of β-phenylpropenyl alcohols by transfer hydrogenation of cinnamaldehyde

[0021] To cinnamaldehyde (2.0mmol), according to the molar ratio of cinnamaldehyde a...

Embodiment 2

[0024] The preparation of the catalyst stock solution is the same as that in Example 1. In cinnamaldehyde (2.0mmol), according to the molar ratio of cinnamaldehyde to formic acid / sodium formate, the molar ratio of cinnamaldehyde to formic acid / sodium formate is 1:20, and 2mol / L formic acid / sodium formate aqueous solution (v / v=7 : 1, pH=2.6) 20mL, the solution was evacuated / nitrogen replaced three times, and then the round bottom flask was frozen in liquid nitrogen under nitrogen protection until the solution was completely frozen as a solid. Then, under vacuum conditions, the round bottom flask was slowly heated in warm water to remove dissolved oxygen and other gases in the aqueous solution. After the solid is completely dissolved, fill it with nitrogen, and perform "liquid nitrogen freezing and degassing-vacuumizing-nitrogen protection thawing" again, repeating three times. Then add the prepared [Cp*Ir(4,4'-(OH) 2 -bpy)(OH 2 )]SO 4 (Ⅴ) Catalyst aqueous solution (1 μmol), ...

Embodiment 3

[0027] The preparation of the catalyst stock solution is the same as that in Example 1. In cinnamaldehyde (2.0mmol), according to the molar ratio of cinnamaldehyde to formic acid / sodium formate, the molar ratio of cinnamaldehyde to formic acid / sodium formate is 1:20, and 2mol / L formic acid / sodium formate aqueous solution (v / v=7 : 1, pH=2.6) 20mL, the solution was evacuated / nitrogen replaced three times, and then the round bottom flask was frozen in liquid nitrogen under nitrogen protection until the solution was completely frozen as a solid. Then, under vacuum conditions, the round bottom flask was slowly heated in warm water to remove dissolved oxygen and other gases in the aqueous solution. After the solid is completely dissolved, fill it with nitrogen, and perform "liquid nitrogen freezing and degassing-vacuumizing-nitrogen protection thawing" again, repeating three times. Then add the prepared [Cp*Ir(6,6'-(OH) 2 -bpy)(OH 2 )]SO 4 (VI) Catalyst aqueous solution (1 μmol),...

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Abstract

The invention belongs to the field of allyl alcohol compounds, and relates to a method for allyl alcohol compounds (II) from alpha,beta-unsaturated aldehyde ketones (I) by transfer hydrogenation, which comprises the following step: by using a metal iridium coordination compound (III) as a catalyst, carrying out transfer hydrogenation reaction on the alpha,beta-unsaturated aldehyde ketones in a formic acid / sodium formate water phase solution. The method provided by the invention is characterized in that the allyl alcohol compounds are prepared by catalyzing the alpha,beta-unsaturated aldehyde ketones in the formic acid / sodium formate water phase. Compared with the reported allyl alcohol compound preparation method, the method provided by the invention uses water as the solvent, and thus, is green, safe, environment-friendly and pollution-free; and meanwhile, the method has the advantages of mild conditions and high product purity, and is simple to operate. The obtained allyl alcohol compounds have very high economic value in the aspects of synthesis of aroma regulators, food flavor additives and drug intermediates, and the like.

Description

technical field [0001] The invention belongs to the field of allyl alcohol compounds, and relates to the preparation of allyl alcohol compounds, in particular to a method for preparing allyl alcohol compounds from α,β-unsaturated aldehydes and ketones. Background technique [0002] The selective reduction product of α,β-unsaturated aldehydes and ketones, allyl alcohols, is an important fine chemical raw material, which has a wide range of applications in the fields of medicine, spices, food additives, and the synthesis of advanced materials. At present, the selective reduction of α,β-unsaturated aldehydes and ketones in industry usually requires hydrogen at a certain temperature and pressure for selective hydrogenation, which has great safety problems. In recent years, the use of non-hydrogen gas as a hydrogen source, safe and easy-to-operate catalytic transfer hydrogenation has attracted increasing attention. [0003] The transfer hydrogenation of α,β-unsaturated aldehydes...

Claims

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Application Information

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IPC IPC(8): C07B41/02C07C29/14C07C33/32C07C201/12C07C205/19C07C253/30C07C255/53
CPCC07B41/02C07C29/14C07C201/12C07C253/30C07C33/32C07C205/19C07C255/53
Inventor 王万辉葛凯包明
Owner DALIAN UNIV OF TECH
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