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Method for preparing homoallylic alcohol

A high allyl alcohol, allyl alcohol technology, applied in the preparation of hydroxyl compounds, organic compounds, chemical instruments and methods, etc., can solve the problems of non-conformity with green chemistry, many side reactions, and inapplicability, and achieve Ease of industrial production, short reaction time, and easy operation

Inactive Publication Date: 2011-05-18
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

All of these methods use organic solvents, some of which require the use of catalysts, low temperature and other conditions; in addition, some methods have many side reactions and low yields, which cannot be applied in practice and do not meet the requirements of green chemistry.

Method used

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  • Method for preparing homoallylic alcohol
  • Method for preparing homoallylic alcohol
  • Method for preparing homoallylic alcohol

Examples

Experimental program
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Embodiment 1

[0021] Embodiment 1, the preparation of 1-(4-methoxyphenyl)-1-hexene-5-en-3-ol

[0022] (1) Activation of magnesium powder: put magnesium powder (2.4g, 0.1mol) and 80mL water into a 100mL round bottom flask equipped with a stirring bar, add 1mL concentrated hydrochloric acid dropwise within one minute and stir. After stirring for 10 min the water was decanted and the metal was washed sequentially with water (3 x 250 mL), acetone (3 x 150 mL) and diethyl ether (3 x 100 mL). Finally, the washed magnesium powder was transferred to a flask equipped with a vacuum conduit and dried in vacuum for three hours. It was used for experiments after cooling.

[0023] (2) Preparation of 1-(4-methoxyphenyl)-1-hexene-5-en-3-ol: add activated magnesium powder (0.096g ), add 4-methoxycinnamaldehyde (0.32g, 2mmol) via dropping funnel, allyl bromide (3mmol), stir at room temperature for 6 minutes; add saturated aqueous ammonium chloride solution (15ml ) after quenching the reaction, extracted w...

Embodiment 2

[0038] Embodiment two, the preparation of 1-(3-chlorophenyl)-3-buten-1-alcohol

[0039] (1) Activation of magnesium powder: with embodiment one.

[0040] (2) Preparation of 1-(3-chlorophenyl)-3-buten-1-ol: add activated magnesium powder (0.096g) and 3-chlorobenzene in a dry reaction flask (50mL round bottom flask) Formaldehyde (0.31g, 2mmol), allyl bromide (3mmol), stirred at room temperature for 5 minutes; after the reaction was completed, saturated ammonium chloride aqueous solution (15ml) was added to the reaction flask to quench the reaction, and extracted with diethyl ether (10ml), Stir for 10 minutes to terminate the reaction; separate the organic phase, extract the aqueous phase with diethyl ether (10mL) for 3 times, and then wash the combined organic phase with MgSO 4 Drying, evaporation of the solvent, and column chromatography (silica gel, 300-400; petroleum ether: ethyl acetate = 15:1), isolated pure product 1-(4-methoxyphenyl)-1-hexene- 5-en-3-ol. Yield: 87%.

[...

Embodiment 3

[0053] Embodiment three, the preparation of 1-(2,6-dichlorophenyl)-3-buten-1-ol

[0054] (1) Activation of magnesium powder: with embodiment one.

[0055] (2) Preparation of 1-(2,6-dichlorophenyl)-3-butene-1-alcohol:

[0056] Add activated magnesium powder (0.096g) and 2,6-dichlorobenzaldehyde (0.38g, 2mmol), allyl bromide (3mmol) into a dry reaction flask (50mL round bottom flask), and stir at room temperature for 5 minutes Add saturated ammonium chloride aqueous solution (15ml) to quench the reaction in the reaction flask after the end of the reaction, extract with diethyl ether (10ml), react under stirring for 10 minutes, and terminate the reaction; separate the organic phase, and use diethyl ether (10mL ) after extraction 3 times, the combined organic phases were washed with MgSO 4 Drying, evaporation of solvent, and column chromatography (silica gel, 300-400; petroleum ether: ethyl acetate = 15: 1), isolated pure product 1-(2,6-dichlorophenyl)-3-butene -1-ol. Yield: 9...

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Abstract

The invention provides a new method for synthesizing homoallylic alcohol. The method comprises the following steps of: making aromatic aldehyde and allyl bromide as raw materials react at room temperataure by using magnesium powder as an accelerator; extracting with diethyl ether and then drying; evaporating out the solvent; and then carrying out column chromatography separation to obtain a single homoallylic alcohol product. The method has the advantages of high productivity and high product quality, wherein the productivity can be higher than 80 percent, and the purity can be higher than 99 percent. In the invention, catalysts and organic solvents are not used, thereby the pollution of the catalysts and the solvents to the environment is reduced, and environmentally friendly chemical synthesis is realized; the reaction is carried out at room temperature, thus the reaction condition is moderate, the reaction time is short, and the efficiency is high; and the method has simple process, is easy and convenient to operate and is easy to realize industrial production.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and relates to a preparation method of homoallyl alcohol, in particular to a method for preparing homoallyl alcohol by using magnesium powder as an accelerator and aromatic aldehyde and allyl bromide as raw materials. Background technique [0002] The chemical structural formula of homoallyl alcohol compound is as follows: [0003] [0004] Among them, R=4-CH 3 O-C 6 h 5 CH=CH 2 , 3-Cl-C 6 h 5 , 2,6-DiCl-C 6 h 5 , 2-Br-C 6 h 5 . [0005] Homoallyl alcohol is an important class of organic compounds, and it is a very important synthetic intermediate in the synthesis of many natural products and bioactive molecules. As a structural unit of many bioactive compounds, it has attracted widespread attention. [0006] At present, there are many reports about the synthesis method of homoallyl alcohol. Wherein the following several methods are widely used: the first method is completed by the...

Claims

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Application Information

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IPC IPC(8): C07C29/38C07C33/48C07C41/30C07C43/23
Inventor 王进贤李顺喜周文俊
Owner NORTHWEST NORMAL UNIVERSITY
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