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Synthetic method of 2, 6-dichloro-4-((4-hydroxyphenyl)amino)phenol

A synthesis method and aminophenol technology are applied in the preparation of amino hydroxy compounds, chemical instruments and methods, preparation of organic compounds, etc., and can solve the problems of low reaction yield, long synthesis steps, and difficult purification, and achieve simple post-processing. , The effect of good product quality and low price

Active Publication Date: 2021-01-08
SHANGHAI MACKLIN BIOCHEM TECH
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Problems solved by technology

[0012] The synthesis idea of ​​this synthesis method is to use 2,6-dichloro-4-aminophenol as a raw material. In the presence of acidic sodium hypochlorite, compound 2 is first obtained, and compound 2 is reacted with phenol in the presence of sodium hydroxide to form a compound 3. Compound 3 was reduced with hydrosulfite to obtain the target compound 4 with a total yield of 46%. The synthesis steps were long, the reaction yield was low, and purification was difficult.

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  • Synthetic method of 2, 6-dichloro-4-((4-hydroxyphenyl)amino)phenol
  • Synthetic method of 2, 6-dichloro-4-((4-hydroxyphenyl)amino)phenol
  • Synthetic method of 2, 6-dichloro-4-((4-hydroxyphenyl)amino)phenol

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[0028] The invention discloses a synthesis method of 2,6-dichloro-4-((4-hydroxyphenyl)amino)phenol, which comprises the following steps:

[0029] Using 2,6-dichloro-4 aminophenol (1.0eq) and phenol (1.0eq) as raw materials, in the presence of 2N NaOH (1.5eq) solution and 6-14% sodium hypochlorite (1.5eq), make it with water 2,6-dichloro-4-((4-hydroxyphenyl)amino)phenol was synthesized in one step using solvent. The chemical reaction formula is as follows:

[0030]

[0031] The preparation method is as follows: 2,6-dichloro-4-aminophenol (1.0eq), phenol (1.0eq), 2N NaOH solution (1.5eq), 6-14% sodium hypochlorite (1.5eq), under nitrogen protection. During the reaction, 2,6-dichloro-4 aminophenol (1.0eq) and phenol (1.0eq) were dissolved in water, and a mixed solvent of 2N NaOH solution (1.5eq) and 6-14% sodium hypochlorite (1.5eq) was added dropwise. After the dropwise addition was completed, the reaction was continued to stir at room temperature for 3 hours.

[0032] The...

Embodiment 1

[0035] In a 250ml reaction flask, add 5.4g of 2,6-dichloro-4-((4-hydroxyphenyl)amino)phenol, 2.82g of phenol, 30ml of water, dropwise add 2N NaOH / 1M NaClO (22.5ml / 55ml ), keep the reaction temperature not higher than 35°C, after the dropwise addition is completed, continue to stir the reaction at room temperature for 3 hours, adjust the system to pH=8 with concentrated hydrochloric acid, filter, pass column purification, and elute with ethyl acetate / petroleum ether=10%, to obtain The target compound p-hydroxydiphenylamine was 5.76g, and the yield was 70.2%.

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Abstract

The invention discloses a synthetic method of 2, 6-dichloro-4-((4-hydroxyphenyl)amino)phenol. The synthetic method comprises the following steps of reacting 1.0 eq of 2, 6-dichloro-4aminophenol and 1.0 eq of phenol under the conditions of 1-3eq of 2N NaOH solution and 1-3eq of 6-14% sodium hypochlorite by taking water as a solvent to synthesize the 2, 6-dichloro-4-((4-hydroxyphenyl)amino)phenol. According to the synthetic method of 2, 6-dichloro-4-((4-hydroxyphenyl)amino)phenol, the target compound is obtained with high yield, the conversion rate is 70% or above, reagents participating in thereaction are easy to obtain, the price is low, aftertreatment is simple and safe, and the product quality is good.

Description

technical field [0001] The invention belongs to the field of p-hydroxydianiline medicinal compound intermediates, and relates to a synthesis method of 2,6-dichloro-4-((4-hydroxyphenyl)amino)phenol. Background technique [0002] The diphenylamine skeleton has a weak basicity (PKb=13.2) because of its nitrogen atom, and the two benzene rings are sterically hindered, so diphenylamine is not easy to form hydrogen bonds with the amino acid residues of the acceptor. Among related structures, diphenyl ether and diphenyl sulfide backbones have less potential because of the impossibility of introducing substituents on heteroatoms. In the case of diphenylmethane, it is more difficult to introduce a substituent on the linker carbon atom, and the aromatic rings are different, and the C-substituted product is a pair of enantiomers, which makes the synthesis more difficult. The advantage of the diphenylamine skeleton is that the linker nitrogen atom can be easily modified by various subs...

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C215/82C07C213/02C07C213/10
CPCC07C213/02C07C213/10C07C215/82
Inventor 董艾能
Owner SHANGHAI MACKLIN BIOCHEM TECH
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