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Method for preparing 2-nitrobenzyl alcohol

A technology of o-nitrobenzyl alcohol and o-nitrophenyl alcohol, applied in the field of preparation of o-nitrobenzyl alcohol, can solve problems such as high energy consumption, and achieve the effects of simple process, simple method and high industrial value

Inactive Publication Date: 2016-07-27
JIANGSU XINHUAI RIVER PHARMTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] This method obtains the final product yield of about 86%, but the reaction process needs to be heated, and the energy consumption is relatively large

Method used

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  • Method for preparing 2-nitrobenzyl alcohol
  • Method for preparing 2-nitrobenzyl alcohol
  • Method for preparing 2-nitrobenzyl alcohol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: 136 grams of 1,2-bis(o-nitrophenyl)ethane (0.50mol) and 324 grams of benzoquinone (3.0mol) were added to a 1000 ml four-necked reaction flask, heated and melted, and stirred React at 135-140°C for 6 hours, track and detect with high performance liquid chromatography; after the reaction, the excess benzoquinone and by-product hydroquinone are recovered under reduced pressure by the water pump; add 408 grams of methanol to the residue to dissolve, and then add 19 grams of boron Sodium hydride (0.5 mol), stirred and reacted at 15°C for 2 hours; after the reduction reaction, the solvent methanol was recovered, and 145.4 grams of the product at 160-165°C / 15mmHg was collected by distillation, which was the target product o-nitrobenzyl alcohol, with a liquid phase content of 94.9%, The yield was 90.2%; recrystallization with toluene gave 125.2 g of pale yellow crystals, mp70-72°C, liquid phase content 99.2%, and total yield 81.1%.

[0026] Product structure verifica...

Embodiment 2～8

[0027] Embodiment 2~8: the preparation condition experiment of o-nitrobenzaldehyde

[0028] Add 136 grams of 1,2-bis(o-nitrophenyl)ethane (0.50mol) and a certain amount of benzoquinone into a 1000 ml four-necked reaction flask, heat and melt, stir at a certain temperature to react, high-efficiency liquid Phase chromatography tracking detection; after the reaction, the excess benzoquinone and by-product hydroquinone were recovered by water pump decompression; 408 grams of methanol was added to the residue to dissolve, and then 19 grams of sodium borohydride (0.5 moles) was added, and stirred at 15°C Reaction for 2 hours; after the reduction reaction, the solvent methanol was recovered, the product was collected by distillation at 160-165°C / 15mmHg, the content was analyzed by liquid phase, and the yield was calculated. The results are shown in the following table.

[0029] .

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Abstract

The invention discloses a method for preparing 2-nitrobenzyl alcohol.According to the method, 1,2-bis(o-nitrophenyl)ethane(13) is taken as the raw material and made to react with benzoquinone; after reaction, an excessive amount of benzoquinone and the byproduct hydroquinone are distilled off; methyl alcohol is added to residues to be dissolved, and then sodium borohydride is added for reduction; after reduction reaction, the solvent methyl alcohol is recycled, and the target product 2-nitrobenzyl alcohol of 160-165 DEG C / 15 mm Hg is collected through distillation.The raw material 1,2-bis(o-nitrophenyl)ethane(13) which is of a symmetrical structure directly reacts with benzoquinone to prepare 2-nitrobenzyl alcohol, the method is simple, the byproduct can be recycled, and industrial value is quite high.

Description

technical field [0001] The invention relates to a pharmaceutical chemical intermediate, in particular to a preparation method of o-nitrobenzyl alcohol. Background technique [0002] O-nitrobenzyl alcohol is an important intermediate in organic synthesis and medicine. Nifedipine, a drug for treating coronary heart disease and angina pectoris, and nifedipine, a drug for hypertension, can be synthesized through o-nitrobenzyl alcohol. The main preparation method is as follows: [0003] 1. Using o-nitrotoluene as a raw material, it first undergoes free radical substitution reaction with bromine under the catalysis of peroxide to obtain o-nitrobenzyl bromide, and then hydrolyzes it under alkaline conditions to obtain o-nitrobenzyl alcohol. The route is as follows: [0004] [0005] The intermediate product o-nitrobenzyl bromide generated in the first step of the method has strong corrosiveness, has high requirements on equipment, and has a low yield, which is reported in the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C201/12C07C205/19C07C205/44
CPCC07C201/12C07C205/19C07C205/44
Inventor 唐鹏飞彭本军白广利彭志刚李铭
Owner JIANGSU XINHUAI RIVER PHARMTECH