Method for synthesizing 3-methoxy nitrobenzene

A technology of methoxynitrobenzene and synthesis method, which is applied in the field of synthesis of organic compounds, can solve the problems of high price and difficult post-processing, and achieve the effects of reducing costs, increasing output, and reducing environmental pollution

Inactive Publication Date: 2008-08-27
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The main disadvantage of this method is that the organic solvent hexamethylphosphoric triamide (HMPA) is expensive, and it causes difficulties in post-processing

Method used

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  • Method for synthesizing 3-methoxy nitrobenzene
  • Method for synthesizing 3-methoxy nitrobenzene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Embodiment 1, a kind of synthetic method of 3-methoxynitrobenzene, carries out following steps successively:

[0015] 1), methoxylation, i.e. the preparation of 3-methoxynitrobenzene crude product:

[0016] 168.0g (1.0mol) m-dinitrobenzene, 135.0g (2.5mol) sodium methylate, 410ml methanol, 0.33g 18-crown-6 ether, 3.36g tetrabutyl bromide were put into an autoclave with stirring and temperature control Ammonium (TBAB), under 1.0 MPa, heated to 150° C. for 10 h to obtain 130.5 g of a dark red solid, which is a crude product of 3-methoxynitrobenzene, and the yield of the crude product was 85.3%.

[0017] 2), recrystallization, i.e. the preparation of 3-methoxynitrobenzene:

[0018] At room temperature, add isopropanol (330 mL) to the above crude 3-methoxynitrobenzene, heat to reflux for 5 h, cool, and vacuum filter. After washing and drying, 121.8 g of white solid was obtained, which was 3-methoxynitrobenzene, and the product yield was 79.6%.

Embodiment 2

[0019] Embodiment 2, a kind of synthetic method of 3-methoxynitrobenzene, carry out following steps successively:

[0020] 1), methoxylation, i.e. the preparation of 3-methoxynitrobenzene crude product:

[0021] 33.6g (0.2mol) m-dinitrobenzene, 21.6g (0.4mol) sodium methoxide, 80ml methanol, 0.02g18-crown-6 ether, 0.17g tetrabutyl bromide were put into the autoclave with stirring and temperature control Ammonium (TBAB), heated at 0.5 MPa to 100° C. for 6.5 h to obtain 26.9 g of a dark red solid, which is a crude product of 3-methoxynitrobenzene, and the yield of the crude product is 87.9%.

[0022] 2), recrystallization, i.e. the preparation of 3-methoxynitrobenzene:

[0023] At room temperature, add n-propanol (100 mL) to the crude 3-methoxynitrobenzene, heat to reflux for 2 h, cool, and vacuum filter. After washing and drying, 25.6 g of white solid was obtained, which was 3-methoxynitrobenzene, and the product yield was 83.6%.

Embodiment 3

[0024] Embodiment 3, a kind of synthetic method of 3-methoxynitrobenzene, carries out following steps successively:

[0025] 1), methoxylation, i.e. the preparation of 3-methoxynitrobenzene crude product:

[0026] 84.0g (0.5mol) m-dinitrobenzene, 34.0g (0.63mol) sodium methylate, 300ml methanol, 0.08g 18-crown-6 ether, 0.84g tetrabutyl bromide were put into the autoclave with stirring and temperature control Ammonium (TBAB), heated at 0.65MPa to 120°C for 5h to obtain 72.7g of a dark red solid, which is a crude product of 3-methoxynitrobenzene, and the yield of the crude product is 95.0%.

[0027] 2), recrystallization, i.e. the preparation of 3-methoxynitrobenzene:

[0028] At room temperature, ethanol (180 mL) was added to the crude 3-methoxynitrobenzene, heated to reflux for 1 h, cooled, and vacuum filtered. After washing and drying, 69.4 g of white solid was obtained, which was 3-methoxynitrobenzene, and the product yield was 90.6%.

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Abstract

The invention discloses a synthesis method of 3-methoxy nitrobenzene, which comprises (1), processing methoxylation that processing methoxylation on m-dinitrobenzene and sodium methoxide in methanol solution in an autoclave, in the presence of 18-crown-6-ether and tetrabutyl bromide catalysts, to obtain crude 3-methoxy nitrobenzene, (2), recrystallizing that recrystallizing the crude 3-methoxy nitrobenzene in liquid alcohol to be reacted in reflux temperature, to obtain 3-methoxy nitrobenzene. The inventive synthesis method of 3-methoxy nitrobenzene has simple process, low cost and environment protection.

Description

technical field [0001] The invention relates to a method for synthesizing organic compounds, in particular to a method for synthesizing 3-methoxynitrobenzene. Background technique [0002] [0003] 3-methoxynitrobenzene with the molecular formula shown in S-1 is widely used in the fields of medicine, organic dyes and pigments, and is an important intermediate for the synthesis of phenothiazine and fluoran thermosensitive dyes. The main synthetic method of 3-methoxynitrobenzene is as reported in literature (Tetrahedron, 1978,34 (14), 2057-2068) in the organic solvent hexamethylphosphoric triamide (HMPA), with m-dinitrobenzene and methanol and potassium phosphate as raw materials to synthesize the target product. The main disadvantage of this method is that the organic solvent hexamethylphosphoric triamide (HMPA) is expensive, and it causes difficulties in post-processing. Contents of the invention [0004] The technical problem to be solved by the present invention is ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C205/37C07C201/12
Inventor 陈新志沙兰兰钱超
Owner ZHEJIANG UNIV
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