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Method for synthesizing 3-methoxybenzaldehyde

A technology of methoxybenzaldehyde and methoxybenzyl alcohol is applied in the synthesis field of 3-methoxybenzaldehyde, can solve the problems of high cost and the like, and achieves the effects of easy operation, environmental friendliness, and cheap and readily available raw materials

Inactive Publication Date: 2009-11-04
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method seems simple, but the raw material m-hydroxybenzaldehyde is expensive relative to m-methoxybenzyl alcohol, and adopts a highly toxic method (during mild poisoning, it is manifested as shyness, tearing, conjunctival hyperemia, cough, expectoration, chest tightness, Moderate poisoning manifests as obvious cough, sputum, shortness of breath, accompanied by chest tightness and mild cyanosis; severe poisoning manifests as a large amount of white or pink foamy sputum, obvious dyspnea, cyanosis, accompanied by suffocation, pneumothorax, and mediastinal gas swelling, subcutaneous emphysema

Method used

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  • Method for synthesizing 3-methoxybenzaldehyde

Examples

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Comparison scheme
Effect test

Embodiment 1

[0015] The molar ratio of nitric acid and m-methoxybenzyl alcohol is 1.5, and the mass ratio of water and m-methoxybenzyl alcohol is 1;

[0016] Lower the two-necked bottle below 5 degrees, then add m-methoxybenzyl alcohol, start stirring, then add the nitric acid solution prepared in advance, after the addition, the system returns to room temperature, TLC and liquid phase monitor the reaction. The system was neutralized by adding sodium hydroxide solution, extracted with dichloromethane, washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The product was obtained by precipitation under reduced pressure. Yield: 94%. 1 HNMR (300M, CDCl 3 ) δ (ppm) 9.87 (s, 1H, CHO), 3.73 (s, 3H, CH 3 ), 7.05(d, 1H, ArH), 7.32-7.37(m, 3H, ArH).

Embodiment 2

[0018] The molar ratio of nitric acid to m-methoxybenzyl alcohol is 1, and the mass ratio of water to m-methoxybenzyl alcohol is 0.8 to 1.5; the steps are the same as in Example 1, and the yield is 71%.

Embodiment 3

[0020] The molar ratio of nitric acid to m-methoxybenzyl alcohol is 2, and the mass ratio of water to m-methoxybenzyl alcohol is 1.5; the steps are the same as in Example 1, and the yield is 73%.

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Abstract

The invention relates to a method for synthesizing 3-methoxybenzaldehyde. M-methoxybenzyl alcohol is used as a raw material; at room temperature, 3-methoxybenzaldehyde is obtained by taking water as a dissolvent and using nitric acid for direct oxidation; and the use level of the nitric acid is 1 to 2 times as that of the m-methoxybenzyl alcohol on a molar basis and the use level of water is 0.8 to 1.5 times that of the m-methoxybenzyl alcohol on a mass basis. The method adopts water as the dissolvent and the nitric acid as an oxidizer to efficiently oxidize the m-methoxybenzyl alcohol into corresponding aldehyde, and has the advantages of simple operation, cheap and easily accessible raw materials, low requirement on equipments, environmental protection, low toxicity, easy post treatment and the like; and furthermore, the cost of the dissolvent is nearly zero. The method meets the requirement of environment-friendly industrial production; therefore, the application prospect of the method is considerably broad.

Description

technical field [0001] The invention belongs to the technical field of preparation and application of fine chemical products, and specifically relates to a synthesis method of 3-methoxybenzaldehyde. Background technique [0002] 3-methoxybenzaldehyde / m-methoxybenzaldehyde / m-anisaldehyde, English name: 3-methoxybenzaldehyde / m-methoxybenzaldehyde / m-anisaldehyde, colorless or light yellow oily liquid, density: 1.119, boiling point: 143°C (50mmHg), Refractive Index: 1.55-1.554, Flash Point: 110°C, Solubility: Insoluble in water, soluble in alcohol, ether, and benzene. CAS: 591-31-1, molecular formula: C 8 h 8 o 2 Molecular weight: 136.15, it is widely used in chemical and chemical industry as chemical raw materials, organic intermediates and spices. The synthetic method of 3-methoxybenzaldehyde as described in the claims belongs to this invention patent. The compound of the present invention is the necessary raw material for the synthesis of isoquinoline and its derivatives...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C47/575C07C45/29
Inventor 徐凤波金艳娟董建兰敖丽华张奉志
Owner NANKAI UNIV
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