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Method for preparing mixture of ortho vanillin and vanillin

An ortho-vanillin and mixture technology, applied in the field of pharmaceutical synthesis, can solve the problems of low reaction conversion rate, low vanillin content, unsuitable for industrial production and the like, and achieve the effect of high weight yield

Inactive Publication Date: 2012-06-27
NORTHEAST PHARMA GRP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Specifically, guaiacol reacts with chloroform under alkaline conditions to generate a mixture of vanillin and ortho-vanillin. The disadvantage of this preparation method is that the reaction conversion rate is low, and the total yield is only about 60%. The content of ortho-vanillin is low, only as a by-product, not suitable for industrial production

Method used

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  • Method for preparing mixture of ortho vanillin and vanillin
  • Method for preparing mixture of ortho vanillin and vanillin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0011] 1. Reaction operation method

[0012] 100 grams of guaiacol, 480 milliliters of methanol, and 66 milliliters of chloroform were added to a 1-liter four-necked flask to obtain a mixed solution, which was stirred and heated to 50° C.; the prepared aqueous sodium hydroxide solution (130 grams of sodium hydroxide (dissolved in 160 ml of water) was slowly added dropwise to the mixed solution, the reaction temperature was controlled at about 55°C, and the dropping process was about 1 hour; PH to 6, filter with suction, wash the filter cake with recovered methanol until it is colorless, and combine the washing liquid and the filtrate.

[0013] 2. Steam methanol

[0014] 40°C water pump decompression distillation evaporated methanol to dryness, layered to separate the upper layer of oil; after washing with water, separated into layers, and separated the oil layer; 60°C diaphragm pump decompressed distillation for 30 minutes, finally obtained oily liquid, weighed, and the ortho...

Embodiment 2

[0018] 1. Reaction operation method

[0019] 80 grams of guaiacol, 400 milliliters of methanol, and 40 milliliters of chloroform were added to a 1-liter four-necked flask to obtain a mixed solution, which was stirred and heated to 50° C.; the prepared aqueous sodium hydroxide solution (100 grams of sodium hydroxide (dissolved in 160 ml of water) was slowly added dropwise to the mixed solution, the reaction temperature was controlled at about 55°C, and the dropping process was about 1 hour; PH to 6, filter with suction, wash the filter cake with recovered methanol until it is colorless, and combine the washing liquid and the filtrate.

[0020] 2. Steam methanol

[0021] 40 ℃ water pump decompression distillation to evaporate methanol to dryness, separate the upper oil layer by layer; separate the layers after washing with water, and separate the oil layer. 60 DEG C diaphragm pump vacuum distillation for 30 minutes, finally obtained oily liquid, weighed, and the total weight y...

Embodiment 3

[0025] 1. Reaction operation method

[0026] 120 grams of guaiacol, 560 milliliters of methanol, and 90 milliliters of chloroform were added to a 1-liter four-neck flask to obtain a mixed solution, which was stirred and heated to 50° C.; the prepared aqueous sodium hydroxide solution (160 grams of sodium hydroxide (dissolved in 160 ml of water) was slowly added dropwise to the mixed solution, the reaction temperature was controlled at about 55°C, and the dropping process was about 1 hour; PH to 6, filter with suction, wash the filter cake with recovered methanol until it is colorless, and combine the washing liquid and the filtrate.

[0027] 2. Steam methanol

[0028] 40°C water pump decompression distillation evaporated methanol to dryness, layered to separate the upper layer of oil; after washing with water, separated into layers, and separated the oil layer; 60°C diaphragm pump decompressed distillation for 30 minutes, finally obtained oily liquid, weighed, and the ortho p...

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Abstract

The invention relates to a method for preparing a mixture of ortho vanillin and vanillin, which is applied to the field of medicine synthesis. The method comprises the following steps of: taking guaiacol and chloroform as raw materials; taking carbinol as a medium; reacting under the condition that sodium hydroxide aqueous solution is added; and utilizing acid to adjust the pH value of the obtained products to be at acid level, thereby obtaining the mixture of ortho vanillin and vanillin, wherein the weight ratio of guaiacol to chloroform to carbinol to sodium hydroxide is (40-60): (200-280): (20-45): (50-80); the concentration of the sodium hydroxide aqueous solution is 40-50%; the reaction temperature in the preparing method is 55 DEG C; the holding time is 4 hours; and the pH value is 5-6. The method further comprises the step of steaming carbinol from the mixture and distilling and removing dregs; the process of steaming carbinol comprises the following steps of: pumping and filtering the mixture, carrying out distilling under reduced pressure by a water pump at 40 DEG C and drying the carbinol, thereby obtaining an oily matter; and the oily matter is subjected to distilling under reduced pressure for 30 minutes at 60 DEG C, thereby obtaining oily liquid. According to the method provided by the invention, the yield of total weight is high and the proportion of the ortho vanillin is increased.

Description

technical field [0001] The invention relates to a preparation method of ortho-vanillin and vanillin mixture in the field of drug synthesis. Background technique [0002] O-vanillin is also known as o-vanillin and o-vanillin. Its chemical name is 2-hydroxy-3-methoxybenzaldehyde, and its English name is o-Vanillin. It can be used as an intermediate in organic synthesis, and it can also be used for electroplating bright Drugs, pharmaceuticals and cosmetics. Ortho-vanillin is pale yellow needle-like crystal, with a melting point of 44-45°C and a boiling point of 265-266°C. It is soluble in ethanol, acetone, chloroform, etc., but insoluble in water. Vanillin, also known as vanillin, has a chemical name of 4-hydroxy-3-methoxybenzaldehyde, and its English name is Vanillin. Vanillin has a wide range of applications in foreign countries. It is widely used in the production of pharmaceutical intermediates, and is also used in plant growth promoters, fungicides, lubricant defoamers, ...

Claims

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Application Information

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IPC IPC(8): C07C45/00C07C47/58
Inventor 杨渐飞杨亚圣王飞董爱军崔振强陈铮
Owner NORTHEAST PHARMA GRP
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