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Method for synthesizing unsaturated primary alcohol in water phase

An unsaturated, water-phase technology, applied in the synthesis of unsaturated primary alcohols, the synthesis of unsaturated primary alcohols, can solve the problems of high reaction temperature, environmental pollution, etc., to achieve high yield, high conversion rate, mild reaction conditions Effect

Active Publication Date: 2021-07-13
上海橡实化学有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In the prior art, there are metal-ligand bifunctional iridium catalysts [Cp*Ir(2,2'-bpyO)(H 2 (0)], select isopropanol for use as solvent and hydrogen source, under neutral conditions by the transfer hydrogenation reaction of unsaturated aldehyde synthesis unsaturated primary alcohol report, in this prior art, take isopropanol as solvent, to the environment Cause certain pollution, and reaction temperature is higher, still have certain deficiency

Method used

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  • Method for synthesizing unsaturated primary alcohol in water phase
  • Method for synthesizing unsaturated primary alcohol in water phase
  • Method for synthesizing unsaturated primary alcohol in water phase

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Synthesis of cinnamyl alcohol 3-Phenylprop-2-en-1-ol, the structural formula is as follows:

[0035]

[0036] The method is: cinnamaldehyde (132 mg, 1.0 mmol), metal iridium complex [Cp*Ir(2,2'-bpyO)(OH)][Na] (4.6 mg , 0.01 mmol, 1 mol%) and Water (1 mL) was successively added to a 5 mL round-bottomed flask, and the air in the round-bottomed flask was replaced with hydrogen, and the pressure of hydrogen in the system was maintained at 1 standard atmosphere during the entire reaction process, and the reaction mixture was The reaction was carried out at 30° C. for 4 hours, 12 hours and 20 hours in a hydrogen atmosphere, respectively. After the reaction, the solvent was removed by rotary evaporation, and then the pure target compound was obtained by column chromatography (developing solvent: petroleum ether: ethyl acetate volume ratio = 8:1). Calculate the product yield based on cinnamaldehyde.

[0037]The NMR spectrum of the obtained product is as figure 2 As shown...

Embodiment 2

[0042] Synthesis of cinnamyl alcohol 3-Phenylprop-2-en-1-ol, the method is: cinnamaldehyde (132 mg, 1.0 mmol), metal iridium complex [Cp*Ir(2,2'-bpyO)(OH)] [Na] (4.6 mg, 0.01 mmol, 1 mol%) and water (1 mL) were successively added to a 5 mL round bottom flask, and the air in the round bottom flask was replaced with hydrogen, and maintained during the entire reaction The pressure of hydrogen in the system was 1 standard atmospheric pressure, and the reaction mixture was reacted at 10°C in a hydrogen atmosphere for 20 h. After the reaction, the solvent was removed by rotary evaporation, and then the pure target compound was obtained by column chromatography (developing solvent: petroleum ether: ethyl acetate volume ratio = 8:1), with a yield of 96%.

Embodiment 3

[0044] Synthesis of cinnamyl alcohol 3-Phenylprop-2-en-1-ol, the method is: cinnamaldehyde (132 mg, 1.0 mmol), metal iridium complex [Cp*Ir(2,2'-bpyO)(OH)] [Na] (4.6 mg, 0.01 mmol, 1 mol%) and water (1 mL) were successively added to a 5 mL round bottom flask, and the air in the round bottom flask was replaced with hydrogen, and maintained during the entire reaction The pressure of hydrogen in the system was 1 standard atmospheric pressure, and the reaction mixture was reacted at 50°C in a hydrogen atmosphere for 12 h. After the reaction, the solvent was removed by rotary evaporation, and then the pure target compound was obtained by column chromatography (developing solvent: petroleum ether: ethyl acetate volume ratio = 8:1), with a yield of 97%.

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Abstract

The invention discloses a method for synthesizing unsaturated primary alcohol in a water phase. The method comprises the following steps: taking unsaturated aldehyde as a raw material, selecting water as a solvent, and carrying out catalytic hydrogenation reaction on the unsaturated aldehyde in the presence of a water-soluble catalyst to obtain the unsaturated primary alcohol, wherein the catalyst is a metal iridium complex [Cp * Ir (2, 2'-bpyO)(OH)][Na]. Water is used as the solvent, so that the use of an organic solvent is avoided, and the method is more environment-friendly; the reaction is carried out at relatively low temperature and normal pressure, and the reaction conditions are mild; alkali is not needed in the reaction, so that generation of byproducts is avoided; and the conversion rate of the raw materials is high, and the yield of the obtained product is high. The method not only has academic research value, but also has a certain industrialization prospect.and.

Description

technical field [0001] The invention relates to a method for synthesizing unsaturated primary alcohols, in particular to a method for synthesizing unsaturated primary alcohols in an aqueous phase with mild reaction conditions, and belongs to the technical field of organic synthesis chemistry. Background technique [0002] Unsaturated primary alcohols are an important class of primary alcohols. The unsaturated bonds in their structures have high chemical reactivity and can undergo chemical reactions such as polymerization, esterification, ionization, substitution, oxidation, and reduction. It is an important organic chemical raw material and has a wide range of application values ​​in the production of resins, spices, plasticizers, drugs, cosmetics and dyes. Traditional synthetic methods mainly use equivalent or excess reducing agents to reduce the C=O bond of unsaturated aldehydes to prepare unsaturated primary alcohols. However, these methods are often accompanied by the g...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C29/141C07C41/26C07B41/02C07C33/32C07C33/30C07C43/23C07C33/48C07C33/14C07C27/04
CPCC07C29/141C07C41/26C07B41/02C07C2601/16C07C33/32C07C33/30C07C43/23C07C33/483C07C33/14
Inventor 王荣周马松邢令宝马德龙孙庆刚潘琳琳王才朋
Owner 上海橡实化学有限公司
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