A kind of synthetic method of m-position alkylphenol
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A technology for an alkyl phenol and a synthesis method, applied in the field of chemistry, can solve the problems of difficult separation, many by-products, complicated and lengthy synthesis steps of meta-alkyl phenol, etc., and achieves the effects of simple reaction and reliable source
Inactive Publication Date: 2018-08-07
ANYANG NORMAL UNIV
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So far, the synthesis steps of meta-alkylphenols are very complicated and tedious, not only have many by-products, but also are difficult to separate
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preparation example 1
[0013] Add 34mg (0.2mmol) 2-phenoxypyridine, 90mg (0.6 mmol) 3-bromopentane, 6mg (0.01mmol) dichlorobis(4-methylisopropylphenyl) into a 20mL pressure-resistant reaction tube Ruthenium, 55mg (0.4mmol) potassium carbonate, 11mg (0.06mmol) 1-adamantanic acid, 1.5mL benzene, sealed under nitrogen, heated to 120°C for reaction, stirred for 24 hours, after reaction, separated by column chromatography to obtain the target product 2-(3-(3-Pentyl)phenoxy) 35 mg, yield 73%.
preparation example 2
[0015] Add 40mg (0.2mmol) 2-(4-methoxyphenoxy)pyridine, 90mg (0.6mmol) 2-bromopentane, 6mg (0.01mmol) dichlorobis(4-methyl) into a 20mL pressure-resistant reaction tube Isopropylphenyl) ruthenium, 55mg (0.4mmol) potassium carbonate, 11mg (0.06mmol) 1-adamantanic acid, 1.5mL benzene, sealed under nitrogen, heated to 120°C for reaction, stirred for 24 hours, after the reaction, After separation by column chromatography, 44 mg of the target product 2-(2-pentyl-4-methoxyphenoxy)pyridine was obtained with a yield of 81%.
preparation example 3
[0017] Add 34 mg (0.2 mmol) of phenoxypyridine, 82 mg (0.6 mmol) of tert-butane bromide, 6 mg (0.01 mmol) of dichlorobis(4-methylisopropylphenyl) ruthenium into a 20 mL pressure-resistant reaction tube, 55mg (0.4mmol) of potassium carbonate, 11mg (0.06mmol) of 1-adamantanic acid, 1.5mL of benzene, sealed under nitrogen, heated to 120°C for reaction, stirred for 24 hours, after reaction, separated by column chromatography to obtain the target product 2- (3-tert-butylphenoxy)pyridine 25 mg, yield 56%.
[0018] The application's m-position alkylphenol preparation embodiment:
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Abstract
Disclosed is a meta-position alkylphenol synthesizing method. The meta-position alkylphenol synthesizing method is obtained through direct reaction of 2-(3-alkyl-phenoxy) pyridine and methyl trifluoromethansulfonate. The method comprises a reaction process of directly adding the 2-(3-alkyl-phenoxy) pyridine, the methyl trifluoromethansulfonate and methylbenzene into a reaction device; in a nitrogen atmosphere, performing stirring at 100 DEG C for reaction for 24 hours, and after the reaction is completed, separating out coarse products; adding the coarse products and sodium into methyl alcohol for refluxing for 15 minutes, and then performing separation to obtain meta-position alkylphenol compounds. The meta-position alkylphenol synthesizing method is reliable in raw material source and simple in reaction and is an economic and efficient meta-position alkylphenol preparing method.
Description
technical field [0001] The invention relates to a preparation process of meta-alkylphenols, in particular to a process for synthesizing meta-alkylphenols from 2-(3-alkylphenoxy)pyridine derivatives, which belongs to the field of chemistry. Background technique [0002] Meta-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. In the traditional electrophilic substitution reaction of aromatic compounds, the phenolic hydroxyl group is the ortho / para substituent, and the alkylation of phenol mainly produces ortho- and para-alkylphenols, while meta-alkylphenols are very difficult to obtain directly . So far, the synthetic steps of meta-alkylphenols are very complicated and tedious, not only have many by-products, but also are difficult to separate. Contents of the invention [0003] The purpose of the present invention i...
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