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Method for converting alkyne into alcohol

An alkyne and acetylene technology, which is applied in the field of formic acid to promote the conversion of alkynes to alcohols, can solve the problems of flammable and explosive handling of hydrogen, harsh reaction conditions, long reaction time, etc., and achieves low production cost, mild reaction conditions and simple operation. Effect

Inactive Publication Date: 2013-07-24
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0003] The preparation methods of alcohols reported in the existing literature mainly include: (1) in the presence of a catalyst, hydrogen is used as a hydrogen source to reduce aldehydes and ketones to generate alcohols. This reaction is usually operated in a reactor, and the pressure of the required hydrogen is relatively high, and Hydrogen is flammable and explosive handling hazards
(2) Prepared by Grignard reagent, the reaction conditions of this method are harsh, and the reaction needs to be operated under anhydrous and oxygen-free conditions; (3) Halocarbons are hydrolyzed to obtain alcohols; (4) Alkynes are hydrogenated to generate alcohols, which use a combination of catalysts to Isopropanol is used as the reaction solvent, and the reaction time is longer

Method used

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  • Method for converting alkyne into alcohol
  • Method for converting alkyne into alcohol
  • Method for converting alkyne into alcohol

Examples

Experimental program
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Effect test

Embodiment 1

[0020] Taking the preparation of phenylethyl alcohol as an example, its structural formula is shown in formula I, where R is H, and the raw materials used and the preparation method are as follows:

[0021]

[0022] Under the protection of argon, add 306mg (3.0mmol) phenylacetylene and 3.5mL formic acid into the thick-walled pressure-resistant tube, the molar ratio of phenylacetylene and formic acid is 1:30, stir, react at 100°C for 0.5 hours, cool to room temperature, Use saturated sodium formate aqueous solution to adjust the pH value to 3~4, add 1.85 mg of (pentamethylcyclopentadiene) chloride-(5-methoxy-2-{1-[(4-methoxyphenyl) Amine iridium, (pentamethylcyclopentadiene)-(5-methoxy-2-{1-[(4-methoxyphenyl)imide) molar ratio of iridium to phenylacetylene is 1:1000 , react at 80°C for 6 hours, add methanol 8 times its volume to the reaction solution, adjust to alkalinity with potassium hydroxide, hydrolyze for 30 minutes, extract with ethyl acetate, dry the organic phase wi...

Embodiment 2

[0025] Taking the preparation of 1-(4-methylphenyl)ethanol as an example, its structural formula is shown in formula I, where R is a methyl group, and the raw materials used and the preparation method are as follows:

[0026] Under argon protection, add 348mg (3.0mmol) p-methylphenylacetylene and 3.5mL formic acid into a thick-walled pressure-resistant tube, the molar ratio of p-methylphenylacetylene and formic acid is 1:30, stir, and react at 100°C for 3 hours, cooled to room temperature, adjusted the pH value to 3-4 with saturated aqueous sodium formate solution, added 3.7 mg of (pentamethylcyclopentadiene) chloride-(5-methoxy-2-{1-[(4-methylcyclopentadiene) Oxyphenyl)imide iridium, (pentamethylcyclopentadiene)-(5-methoxy-2-{1-[(4-methoxyphenyl)imide iridium chloride and p-methyl The mol ratio of phenylacetylene is 1:500, 80 ℃ of reactions 6 hours, other steps are identical with embodiment 1, are prepared into 1-(4-methylphenyl) ethanol, and its productive rate is 85%, and t...

Embodiment 3

[0028] Taking the preparation of 1-(4-bromophenyl)ethanol as an example, its structural formula is shown in formula I, where R is Br, and the raw materials used and the preparation method are as follows:

[0029] Under the protection of argon, add 543mg (3.0mmol) p-bromophenylacetylene and 3.5mL formic acid into the thick-walled pressure-resistant tube, the molar ratio of p-bromophenylacetylene and formic acid is 1:30, stir, and react at 100°C for 5 hours. Cool to room temperature, adjust the pH value to 3-4 with saturated aqueous sodium formate solution, add 3.7 mg of (pentamethylcyclopentadiene)-(5-methoxy-2-{1-[(4-methoxy Phenyl)imide iridium, (pentamethylcyclopentadiene)-(5-methoxy-2-{1-[(4-methoxyphenyl)imide iridium chloride and p-bromophenylacetylene Molar ratio is 1:500, 80 ℃ of reaction 6 hours, other steps are identical with embodiment 1, are prepared into 1-(4-bromophenyl) ethanol, and its productive rate is 86%, and the spectral data of product is: 1 H NMR (CDCl ...

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Abstract

The invention discloses a method for converting alkyne into alcohol. The method comprises the following steps of: under the protection of argon, reacting phenylacetylene, p-methyl phenylacetylene, p-bromo phenylacetylene, m-chloro phenylacetylene or di-phenylacetylene with formic acid under the catalysis of chloro(pentamethyl cyclopentadiene)-(5-methoxy-2-{1-[(4-methoxyphenyl)imine iridium or [N-[(1R,2R)-2-(amino-)-1,2-diphenethyl]-4-methylbenzene sulfonamide-N]chloro(pentamethyl cyclopentadiene)-ruthenium; and adjusting the pH value to 3-4 or neutrality to obtain achiral alcohol and chiral alcohol. The method disclosed by the invention has the advantages of easiness in operation, mild reaction conditions, little environmental pollution, high yield and low production cost, and can be applied to industrial production.

Description

technical field [0001] The invention belongs to the technical field of alcohol preparation, and in particular relates to a method for formic acid to promote the conversion of alkyne to generate alcohol (chiral and achiral). Background technique [0002] Alcohols are very important compounds that have a special place in everyday life. Alcohol can be used as beverage, fuel, medical or industrial raw material, and alcohol gel can also be made into hand sanitizer. In addition to extracting from natural plants, alcohol can also be obtained through synthetic methods. Reduction via carbonyl compounds is one of the common methods and has been extensively developed. [0003] The preparation methods of alcohols reported in the existing literature mainly include: (1) in the presence of a catalyst, hydrogen is used as a hydrogen source to reduce aldehydes and ketones to generate alcohols. This reaction is usually operated in a reactor, and the pressure of the required hydrogen is rela...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C29/16C07C33/22C07C33/20C07C33/46C07C33/24
Inventor 王超李佳肖建良薛东
Owner SHAANXI NORMAL UNIV
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