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Preparation method of p-methoxyacetophenone

A technology of methoxyacetophenone and p-methoxybenzene is applied in the field of chemical reagent preparation, can solve problems such as environmental pollution, and achieve the effects of low price, simple operation process and few by-products

Inactive Publication Date: 2014-05-07
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The heavy metal mercury will cause great pollution to the environment

Method used

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  • Preparation method of p-methoxyacetophenone

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[0013] A kind of preparation method of p-methoxyacetophenone proposed by the present invention, add p-methoxyphenylacetylene, tetrakistriphenylphosphine palladium, hydrochloric acid, solvent, the mole of methoxyphenylacetylene and hydrochloric acid successively in the reactor The ratio is 1:1.2, reacted at room temperature for 48 hours, evaporated to dryness, and purified by column chromatography to obtain a light yellow solid product, which is pure p-methoxyacetophenone, and the eluent for column chromatography purification is ethyl acetate The volume ratio of ester to petroleum ether is 1:5.

[0014] In addition, tetrakistriphenylphosphine palladium is a catalyst, and tetrakistriphenylphosphine palladium is 20 mol% of p-methoxyphenylacetylene. The solvent can be selected from anhydrous methanol, anhydrous acetonitrile, and anhydrous dioxane. The reactor is a dry and clean Schlenk bottle, and the Schlenk bottle adopts standard technology, and the whole reaction is carried ou...

Embodiment 1

[0018] Using a dry and clean Schlenk bottle as a reactor, add p-methoxyphenylacetylene (26 μL, 0.2 mmol) and 5 mol / L hydrochloric acid solution (48 μL, 0.24 mmol) under standard Schlenk technique (argon protection), four three Phenylphosphinepalladium (46mg, 0.04mmol) and 3ml of anhydrous methanol. The reaction was stopped after 48 hours at room temperature. The solvent was evaporated to dryness and purified by column chromatography (eluent: ethyl acetate: petroleum ether = 1:5) to obtain pure p-methoxyacetophenone with a yield of 29 mg and a yield of 97%. product by 1 H NMR, 13 Confirmed by C NMR, IR, HRMS. 1 H NMR (400MHz, CDCl 3 )δ2.56(S,3H),3.87(S,3H),6.94(d,J=9.0Hz,2H),7.94(d,J=9.0Hz,2H). 13 C NMR (100MHz, CDCl 3 )δ26.3, 55.4, 113.7, 130.4, 130.6, 163.5, 196.7.

Embodiment 2

[0020] Using a dry and clean Schlenk bottle as a reactor, add p-methoxyphenylacetylene (26 μL, 0.2 mmol) and 5 mol / L hydrochloric acid solution (48 μL, 0.24 mmol) under standard Schlenk technique (argon protection), four three Phenylphosphine palladium (46mg, 0.04mmol) and 3ml of anhydrous acetonitrile. The reaction was stopped after 48 hours at room temperature. The solvent was evaporated to dryness and purified by column chromatography (eluent: ethyl acetate: petroleum ether = 1:5) to obtain pure p-methoxyacetophenone with a yield of 27 mg and a yield of 90%.

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Abstract

The invention provides a preparation method of p-methoxyacetophenone. The preparation method comprises the steps of sequentially adding p-methoxyphenyl acetylene, tetrakis (triphenyl phosphine)palladium, hydrochloric acid and a solvent into a reactor, wherein the mole rate of methoxyphenyl acetylene to hydrochloric acid is 1:1.2; reacting at room temperature for 48h; evaporating the solvent; purifying through filtration column chromatography to obtain a light yellow solid product, namely pure p-methoxyacetophenone, wherein ethyl acetate is used as an eluting agent for column chromatography purification, and the volume ratio of ethyl acetate to petroleum ether is 1:5. Methoxyphenyl acetylene is used as a raw material, so that the raw material is low in price; an experiment can be carried out at room temperature, the operation process is simple, and few side products are generated in the experiment and are easy to separate; the preparation method is novel in design, is a good design scheme and has a certain market promotion prospect.

Description

technical field [0001] The invention relates to a preparation method of chemical reagents, in particular to a preparation method of p-methoxyacetophenone. Background technique [0002] P-methoxyacetophenone is a white crystal with the aroma of hawthorn flower and anisaldehyde. It is soluble in ethanol and ether and cannot be swallowed. It is irritating to eyes and skin. P-methoxyacetophenone is stable to alkali. It is mainly used in soap essence instead of anisaldehyde, and has a broad market and development prospect. [0003] The hydration reaction of alkynes to form carbonyl compounds is one of the most important and basic methods for functional group transformation in organic synthesis. The most commonly used method is to hydrate alkynes smoothly in the presence of excess HgO and sulfuric acid using methanol in aqueous solution as the reaction medium. The heavy metal mercury will cause great pollution to the environment. Most of the other hydration reaction methods nee...

Claims

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Application Information

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IPC IPC(8): C07C49/84C07C45/26
CPCC07C45/26C07C49/84
Inventor 郝新奇牛俊龙李函刘超莉宋毛平
Owner ZHENGZHOU UNIV
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