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Method for preparing phenol through efficient standard hydroxylation of phenylboronic acid

A technology of phenylboronic acid and hydroxylation, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of metal loss and cost increase, and achieve the effect of easy separation and high yield

Active Publication Date: 2018-11-02
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In the reaction system of one-step hydroxylation of phenylboronic acid, metal catalysts are generally required [Chin.J.Org.Chem., 2016,36,862-866; Tetrahedron Lett.,2017,58(45), 4255-4259; Tetrahedron Lett .,2017,58(12),1211-1215; J.Organomet.Chem.,2017,851,52-56], the existence of metal catalysts increases the cost, and there are problems such as metal loss

Method used

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  • Method for preparing phenol through efficient standard hydroxylation of phenylboronic acid
  • Method for preparing phenol through efficient standard hydroxylation of phenylboronic acid
  • Method for preparing phenol through efficient standard hydroxylation of phenylboronic acid

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Embodiment 1

[0022] 5 mmol of phenylboronic acid, 5 mmol of sodium perborate and 5 mmol of additive sodium bicarbonate were added to the reactor with 10 mL of water. At 25°C, phenylboronic acid, sodium perborate and a weak base were dissolved in water, stirred and reacted at a certain temperature for 30 minutes, and then the reaction solution was acidified to pH 3-4, separated, and the yield of phenol was 92.3%.

Embodiment 2

[0024] 5 mmol of phenylboronic acid, 5 mmol of sodium perborate and 5 mmol of additive sodium bicarbonate were added to the reactor with 10 mL of methanol. At 25°C, phenylboronic acid and sodium perborate were dissolved in methanol, stirred and reacted at a certain temperature for 30 minutes, and then the reaction liquid was acidified to pH 3-4, separated, and the yield was 91.6%.

Embodiment 3

[0026] Add 5mmol of phenylboronic acid and 4mmol of sodium perborate into a reactor with 10mL of water, and react for 30min at 25°C. Then the reaction solution was acidified to pH 3-4 and separated to obtain a yield of 74.1%.

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Abstract

The invention discloses a method for preparing phenol through efficient standard hydroxylation of phenylboronic acid. Phenylboronic acid and sodium perborate are added to a solvent and stirring is carried out directly in an alkaline condition or acid condition or with no additive, to obtain phenol. The synthesis method disclosed by the invention is simple and efficient, and the common sodium perborate is used as an oxidant, no catalyst is needed, and phenol can be directly and efficiently synthesized under mild conditions.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for preparing phenol by efficient in-situ hydroxylation of phenylboronic acid. Background technique [0002] Phenolic compounds play an important role in the prevention and treatment of various diseases. Efficient synthesis of phenol is one of the important tasks in organic chemistry. The synthesis of phenol from phenylboronic acid has received extensive attention in organic synthesis. Phenylboronic acid has low toxicity and high stability in the air, and can be directly purchased in the market at a low price. Oxygen and hydrogen peroxide are generally used as oxidants for the in situ hydroxylation of phenylboronic acid to prepare phenol [Appl.Catal.A Gen., 2013, 466, 60-67; Appl.Catal.A:Gen, 2018, 562, 58-66]. Sodium perborate is an ideal oxidant, which has the advantages of few by-products, high selectivity, and low price, and is widely used in...

Claims

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Application Information

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IPC IPC(8): C07C39/04C07C37/055C07F5/02
CPCC07C37/055C07F5/025C07C39/04
Inventor 王伟涛姜旭禄唐皓马养民姜秀芳
Owner SHAANXI UNIV OF SCI & TECH