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Method for preparing alcohol compounds by amine compounds

A technology for amine compounds and aldehyde compounds, which is applied in the field of preparing alcohol compounds from amine compounds, achieves the effects of simple operation process, avoiding strong acid system and high yield

Active Publication Date: 2014-06-11
长兴宜生药物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, the diazotization reaction is affected to a certain extent in the application of aliphatic amines into hydroxyl-substituted compounds or alcohol compounds, and there are few relevant literature reports.

Method used

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  • Method for preparing alcohol compounds by amine compounds
  • Method for preparing alcohol compounds by amine compounds
  • Method for preparing alcohol compounds by amine compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Add acetophenone (48.00g, 0.40mol) in 500mL there-necked flask, benzaldehyde (21.20g, 0.20mol), isopropylamine (11.80g, 0.20mol) and aluminum chloride (1.40g, 10.00mmol), in The reaction was carried out at 30°C without solvent, followed by TCL. After the reaction was completed, it was filtered, and the filtrate was distilled to obtain the corresponding product isopropanol, which was detected by gas chromatography with a purity of 98% and a yield of 80%.

Embodiment 2

[0037] Add acetophenone (72.00g, 0.60mol) in 500mL there-necked flask, benzaldehyde (21.20g, 0.20mol), n-butylamine (14.60g, 0.20mol) and L-proline trifluoromethanesulfonate ( 2.64g, 10.00mmol), reacted under the reflux condition of ethanol (100.00mL), followed by TCL. After the reaction was completed, the product was filtered, and the filtrate was rectified to obtain the corresponding product n-butanol, which was detected by gas chromatography with a purity of 97% and a yield of 93%.

Embodiment 3

[0039] Add p-methylacetophenone (80.40g, 0.60mol), benzaldehyde (21.20g, 0.20mol), glycine (15.00g, 0.20mol) and diphenylamine trifluoromethanesulfonate (3.20mol) in a 500mL three-necked flask g, 10.00 mmol), reacted at 150°C under solvent-free conditions, and followed the reaction with TCL. After the reaction was completed, the product was filtered, and the filtrate was distilled to obtain the product 2-hydroxyacetic acid, which was detected by gas chromatography with a purity of 93% and a yield of 90%.

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Abstract

The invention relates to a novel method for converting amine into corresponding alcohol compounds by a one-pot method. The preparation method comprises the following steps that: ketone, aldehyde and amino compounds are added into a reaction bottle, a certain number of catalysts are added, and heating reaction is carried out under the organic solvent condition or the solvent-free condition to remove amino groups for obtaining the corresponding alcohol compounds. After the reaction is completed, crude products of the products can be obtained only through simple filtering and separation after the reaction is completed, and purified products can be obtained through the distillation of the alcohol compounds. The use of excessive strong acid is avoided through the synthesis route, the reaction conditions are mild, the reaction does not need to be carried out under slow temperature, the energy consumption is saved, and the method is particularly applicable to the fat-type amino compounds and has the advantages that the side reactions are few, the yield is high, and the like.

Description

(1) Technical field [0001] The present invention relates to a novel method for converting amine compounds into corresponding alcohol compounds in one pot. (2) Background technology [0002] Aromatic, aliphatic and heterocyclic primary amines react with nitrous acid (in a strong acid medium) to generate diazonium salts, and diazonium salts replace diazo groups with hydroxyl groups under strong acid and heating conditions to obtain corresponding phenols, alcohols and other hydroxyl compounds , which is an important way to obtain hydroxyl compounds. But the used diazotization reagent sodium nitrite and strong acid (as sulfuric acid, hydrochloric acid) in the diazotization reaction process are all greatly excessive, and this has just brought bigger pressure to the post-reaction treatment, and has caused serious damage to the environment. Big burden. In addition, the diazotization reaction is mostly carried out at low temperature, and the energy consumption is relatively large....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C29/00
Inventor 李坚军俞传明何平苏为科
Owner 长兴宜生药物科技有限公司
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