Preparation method of ortho-alkylphenol

A technology of ortho-alkylphenol and alkylphenoxy, which is applied in the field of chemistry, can solve the problems affecting the synthesis efficiency of ortho-alkylaniline compounds, waste of raw materials, etc., and achieves an easy-to-implement, simple route and few side reactions Effect

Inactive Publication Date: 2018-12-25
ANYANG NORMAL UNIV
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

These two types of synthesis methods are relatively mature and perfect, and have been widely used in laboratory synthesis and chemical industry production. However, in these two types of methods, a large number of para-alkylphenol by-products are generated, which not only seriously affects the ortho-position The synthetic efficiency of alkyl aniline compound, and can cause the waste of raw material, a large amount of by-products appear

Method used

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  • Preparation method of ortho-alkylphenol
  • Preparation method of ortho-alkylphenol
  • Preparation method of ortho-alkylphenol

Examples

Experimental program
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Effect test

Embodiment 1

[0011] Add 2-(2--hexyl)phenoxy)pyridine 255mg (1 mmol), methyl trifluoromethanesulfonate 328mg (2mmol), toluene 10 mL in the reaction tube, under nitrogen, 100 o C stirred for 24 hours, after the reaction, the crude product was separated, then added to the reaction tube, added sodium metal (15mmol) and methanol (15mL), refluxed for 15 minutes, cooled, and separated by column chromatography to obtain 128mg of the target product 2-hexylphenol, The yield was 72%.

Embodiment 2

[0013] Add 275 mg (1 mmol) of 2-(2-phenethylphenoxy)pyridine, 328 mg (2 mmol) of methyl trifluoromethanesulfonate, and 10 mL of toluene to the reaction tube. Under nitrogen, 100 o C stirred for 24 hours. After the reaction, the crude product was separated, then added to the reaction tube, added sodium metal (15mmol) and methanol (15mL), refluxed for 15 minutes, cooled, and separated by column chromatography to obtain the target product 2-phenethylphenol 154 mg, yield 78%.

Embodiment 3

[0015] Add 2-(2-(ethoxyethyl)phenoxy)pyridine 243mg (1 mmol), methyl trifluoromethanesulfonate 328mg (2 mmol) and toluene 10 mL in the reaction tube, under nitrogen, 100 o C stirred for 24 hours, after the reaction, the crude product was separated, then added to the reaction tube, added sodium metal (15mmol) and methanol (15mL), refluxed for 15 minutes, cooled, and separated by column chromatography to obtain the target product 2-ethoxyethyl Base phenol 115mg, productive rate is 69%.

[0016] The following are the synthetic products and corresponding yields using the technical scheme of the present invention.

[0017]

[0018] In the present invention, 2-(2-alkylphenoxy)pyridine derivatives are prepared by using 2-phenoxypyridine derivatives and bromoalkane, which is a primary bromoalkane, and the reaction formula is as follows:

[0019]

[0020] Where: R is an alkyl group or an aryl group or an ether group, and 2-phenoxypyridine derivatives, primary brominated alkanes...

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Abstract

The invention relates to a preparation method of ortho-alkylphenol. A 2-(2-alkylphenoxy) pyridine derivative is used as a raw material to prepare the ortho-alkylphenol. The reaction process includes:directly adding the 2-(2-alkylphenoxy) pyridine derivative, methyl trifluoromethansulfonate and methylbenzene in a reaction device; reacting for 24 h; separating a coarse product; then adding the coarse product in methanol; adding sodium; refluxing for 15 minutes; and separating to obtain the ortho-alkylphenol. The preparation method is simple in route and easy to implement, and side reactions areless in a preparation process.

Description

technical field [0001] The invention relates to a preparation method of ortho-alkylphenols, in particular to a method for synthesizing ortho-alkylphenols from 2-(2-alkylphenoxy)pyridine derivatives, which belongs to the field of chemistry. Background technique [0002] Ortho-alkylphenols are an important class of compounds, which not only widely exist in marketed drugs, pesticides, and natural products with biological activity, but also are a key intermediate in organic synthesis. There are two traditional synthetic routes: one is the electrophilic Friedel-Crafts alkylation of aromatic rings of phenol derivatives and alkyl halides; replace. These two types of synthesis methods are relatively mature and perfect, and have been widely used in laboratory synthesis and chemical industry production. However, in these two types of methods, a large number of para-alkylphenol by-products are generated, which not only seriously affects the ortho-position The synthetic efficiency of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C37/055C07C39/06C07C39/15C07C41/26C07C43/178
CPCC07C37/055C07C41/26C07C39/06C07C39/15C07C43/178
Inventor 李刚杨素玲刘雷雷邢云朱彪
Owner ANYANG NORMAL UNIV
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