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Catalytic oxidation synthetic method of benzoic acid compound

A benzoic acid, catalytic oxidation technology, applied in the preparation of organic compounds, organic chemistry methods, chemical instruments and methods, etc., can solve problems such as the difficulty of benzoic acid compounds

Active Publication Date: 2018-11-16
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Generally speaking, it is more difficult to use the secondary benzyl alcohol to directly cleavage the carbon-carbon bond for the preparation of benzoic acid compounds

Method used

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  • Catalytic oxidation synthetic method of benzoic acid compound
  • Catalytic oxidation synthetic method of benzoic acid compound
  • Catalytic oxidation synthetic method of benzoic acid compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1: the preparation of benzoic acid (formula (2-1))

[0023] Add 1mmol of 1-phenylethanol (formula (1-1)), 0.1mmol of I to a 25mL glass tube equipped with a magnetic stirring bar 2 , 0.1mmol of Fe(NO 3 ) 3 9H 2 O. 2mL of DMSO, replace the air in the glass tube with oxygen and seal the glass tube, then put the sealed glass tube into an oil bath pre-heated to 130°C, and turn on the magnetic stirrer, after 12 hours of reaction, take out the sealed glass tube, wait for it to cool to room temperature, add water to the reaction solution to quench the reaction, then adjust the pH to about 11 with a sodium hydroxide solution with a concentration of 0.1mol / L, wash with ethyl acetate three times, and use a concentration of 0.1mol / L for the aqueous phase / L of hydrochloric acid solution to adjust the pH value to about 2, then extract three times with ether, combine the three ether extracts, distill off the ether under reduced pressure, and then separate by column chro...

Embodiment 2

[0024] Embodiment 2: the preparation of benzoic acid (formula (2-1))

[0025] The reaction steps are the same as in Example 1, except that the reaction time is 16 h, and the isolated yield of benzoic acid is 74%.

Embodiment 3

[0026] Embodiment 3: the preparation of benzoic acid (formula (2-1))

[0027] The reaction steps are the same as in Example 1, except that the reaction time is 8 hours, and the isolated yield of benzoic acid is 66%.

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PUM

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Abstract

The invention discloses a catalytic oxidation synthetic method of a benzoic acid compound. According to the invention, secondary benzylalcohol is used as a reaction substrate, iodine and Fe(NO3)3.9H2Oare used as a catalyst, under oxygen atmosphere of atmospheric pressure, in dimethyl sulfoxide (DMSO), the materials are reacted for 8-16 h at the temperature of 110-140 DEG C, and after the reactionis completed, performing separating processing to obtain the benzoic acid compound. The synthetic method uses an iron-based catalyst which is friendly to environment, a green oxidizing agent oxygen which is friendly to environment is used, the reaction is carried out under normal pressure, and pressurization equipment is not required.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a catalytic oxidation synthesis method of benzoic acid compounds. Background technique [0002] Benzoic acid compounds are important synthetic building blocks in organic synthesis and are key structural units of many natural products, medicines, pesticides, polymers and dyes. Because the carboxyl group contained in it has the ability to transform into other important functional groups such as ester group, acyl halide group, amide group and acid anhydride group, so benzoic acid compounds are also important intermediates in organic synthesis. There are many methods for the synthesis of benzoic acid compounds, and the most studied or reported method is to directly oxidize methyl aromatic hydrocarbons into benzoic acid compounds as raw materials. Stoichiometric metal oxidants such as potassium dichromate, potassium permanganate, or chromium trioxide can be used for the dir...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B41/08C07C51/245C07C63/06C07C63/04C07C63/70C07C65/21C07C201/12C07C205/57C07C253/30C07C255/57C07D333/40C07D307/68
CPCC07B41/08C07C51/245C07C201/12C07C253/30C07D307/68C07D333/40C07C63/06C07C63/04C07C63/70C07C65/21C07C205/57C07C255/57
Inventor 李美超王煜茹徐亮沈振陆
Owner ZHEJIANG UNIV OF TECH