Preparation method of p-nitro-o-cresol

A technology of nitro-o-cresol and nitro-o-cresol, applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry, etc., can solve the problems of low yield of nitro-o-cresol and many reaction by-products , to achieve high purity, easy operation and good repeatability

Inactive Publication Date: 2016-06-22
SHANGHAI VETERINARY RES INST CHINESE ACAD OF AGRI SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to overcome defects such as the low yield of existing synthetic p-nitro-o-cresol and many reaction by-products, and find that p-nitro-o-toluidine is hydrolyzed in alkaline solution to obtain high-purity solid p-nitro-o-cresol phenol, thereby providing a high-yield, easy-to-operate high-purity p-nitro-o-cresol preparation method

Method used

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  • Preparation method of p-nitro-o-cresol
  • Preparation method of p-nitro-o-cresol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Add 60.8g of p-nitro-o-toluidine (0.4mol), 200g of sodium hydroxide and 600ml of water into a 2000ml four-necked flask equipped with a thermometer, a stirrer, and a reflux condenser, heat to 115°C and keep the reaction for 24 hours Then stop heating, add 500ml of water, filter, slowly add hydrochloric acid to the filtrate to adjust the pH of the reaction solution to about 4, and precipitate a yellow solid, wait to cool to room temperature and filter, filter and wash the filter cake three times with 1000ml of water, drain, and store at 50°C Dry in a vacuum oven for 4 hours to obtain a yellow p-nitrophenol solid with a yield of 98.1%, qualitative by mass spectrometry, ESI-MS (m / z): 152.0 [M-H] - ( figure 1 ); Determination of its content by HPLC method, from Table 1 and figure 2 It can be known that the present embodiment p-nitro-o-cresol content is 99.12%.

[0024] Table 1 Peak results

[0025] .

Embodiment 2

[0027] Add 30.4g of p-nitro-o-toluidine (0.2mol), 100g of sodium hydroxide and 900ml of water into a 2000ml four-necked flask equipped with a thermometer, agitator, and reflux condenser, heat to reflux, and stop after reflux for 50 hours Heat, add 500ml of water, filter, slowly add sulfuric acid to the filtrate to adjust the pH of the reaction solution to about 3, precipitate a yellow solid, wait to cool to room temperature, filter, filter, wash the filter cake with 1000ml of water three times, drain, and vacuum dry at 50°C Dry in the oven for 4 hours to obtain a yellow p-nitrophenol solid, yield 98.5%, qualitative by mass spectrometry, ESI-MS (m / z): 152.0 [M-H] - ( image 3 ), using HPLC method to determine its content, from Table 2 and Figure 4 It can be seen that the present embodiment p-nitro-o-cresol content is 99.39%.

[0028] Table 2 Peak results

[0029] .

Embodiment 3

[0031] Add 6.08g of p-nitro-o-toluidine (0.04mol) and 20g of potassium hydroxide and 380ml of water into a 1000ml four-necked flask equipped with a thermometer, a stirrer and a reflux condenser, heat to 95°C and keep the reaction for 72 hours Then stop heating, filter, slowly add phosphoric acid to the filtrate to adjust the pH of the reaction solution to about 5, and precipitate a yellow solid. After cooling to room temperature, filter, wash the filter cake with 100ml water for three times, drain, and place in a vacuum oven at 50°C. Dry for 4 hours to obtain p-nitrophenol, yield 96.5%, ESI-MS (m / z): 152.0[M-H] - ( Figure 5 ), using HPLC method to determine its content, from Table 3 and Figure 6 It can be known that the present embodiment p-nitro-o-cresol content is 99.03%.

[0032] Table 3 Peak results

[0033] .

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Abstract

The invention discloses a preparation method of p-nitro-o-cresol. According to the method, p-nitro-o-cresol is prepared from p-nitro-o-toluidine as a raw material through basic hydrolysis. Obtained p-nitro-o-cresol has high purity, through determination with HPLC (high performance liquid chromatography) and quantification with an area normalization method, the content is 99% or higher, and the yield is 95% or higher; the preparation method is simple and convenient to operate, the preparation method are repeated for multiple times under the process conditions of the method, and the repeatability is good.

Description

technical field [0001] The invention relates to the technical field of fine chemical products, more specifically, the invention relates to a preparation method of p-nitro-o-cresol. Background technique [0002] p-nitro-o-cresol is an important fine chemical intermediate. For example, the international patent WO2015016373A1 publicly reported that p-nitro-o-cresol was used as an intermediate to prepare a series of tetrazolinone compounds as pesticides; In the Chinese invention patent application CN104557688A, it is reported that p-nitro-o-cresol is used to synthesize an intermediate of a novel multi-targeted drug for treating tumors, sorafenib. In addition, p-nitro-o-cresol also has a certain biological activity. For example, it was reported in the Czech patent CzechCS218346B1 published in 1985 that it has a plant growth-promoting effect in combination with aminobenzoic acid. [0003] The reaction starting materials used in the synthesis of p-nitro-o-cresol reported in the li...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C201/12C07C205/22
CPCC07C201/12C07C205/22
Inventor 张丽芳薛飞群朱建德费陈忠王米王霄旸郑文丽张可煜王春梅
Owner SHANGHAI VETERINARY RES INST CHINESE ACAD OF AGRI SCI
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