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Method for preparing 3,4,5-triethoxy methylbenzene

A technology for the oxidation of trimethoxytoluene and methoxy, which is applied in the direction of ether preparation, ester reaction to prepare ether, chemical instruments and methods, etc., can solve the problems of expensive catalysts, long reaction routes, equipment corrosion, etc., and meet the requirements of reaction equipment and reaction conditions Not high, good environmental friendliness, short reaction cycle effect

Inactive Publication Date: 2014-06-18
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The methods for synthesizing 3,4,5-trimethoxytoluene reported in the current literature are as follows: (1) Using p-cresol as raw material, sulfonation reaction occurs under the action of oleum to prepare 2,6-disulfonic acid group -4-methylphenol, and then undergo alkali fusion, and react with dimethyl sulfate to synthesize 3,4,5-trimethoxytoluene. This method needs to consume a large amount of acid and alkali, which seriously corrodes the equipment and causes environmental pollution. Yield is low; (2) take 3,4,5-trimethoxybenzaldehyde as raw material, hydrogenation synthesis 3,4,5-trimethoxytoluene under Pd / C catalysis, although the yield of this method is relatively high High, but the reaction cycle is long, the preparation of raw materials is complicated, the catalyst is expensive, and the production cost is high; (3) using p-cresol as raw material, after bromination and methoxylation in sequence, the methoxylation reaction of ArO- Preparation of 3,4,5,-trimethoxytoluene, the method has a long reaction route, and the separation of methoxylation and ArO-methoxylation reactions is cumbersome

Method used

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  • Method for preparing 3,4,5-triethoxy methylbenzene
  • Method for preparing 3,4,5-triethoxy methylbenzene
  • Method for preparing 3,4,5-triethoxy methylbenzene

Examples

Experimental program
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Effect test

Embodiment 1

[0023] Bromination reaction: The reactor is equipped with a stirrer, 2 balanced dropping bottles, a thermometer and a cold and heat exchanger. Add 138.2g of 4-methylguaiacol with a content of 99%, 400ml of dichloromethane, and 2g of PEG-600 into the reactor, stir and cool to about 0°C, and slowly alternately add 120ml of 30% hydrogen peroxide and 180g of 46% industrial Hydrobromic acid solution, keep stirring at -5°C-5°C for reaction, drop it in about 8 hours, and then react for 1 hour. Stop stirring, and after standing for 30 minutes, separate the upper layer of waste water and discard it; the lower layer of oil is stirred with 10ml of 5% sodium carbonate solution for 1 hour to wash and neutralize to obtain the oil of lower layer pH=6. The dichloromethane solvent was recovered by distillation, and finally about 215 g of white or light red solid (ie 4-methyl-2-bromo-6-methoxyphenol) was obtained.

[0024] Alkylation reaction: In the reactor, add 215g of the solid obtained in ...

Embodiment 2

[0027] Bromination reaction: The reactor is equipped with a stirrer, 2 balanced dropping bottles, a thermometer and a cold and heat exchanger. Add 153.6g of 4-methylguaiacol with a content of 90%, 400ml of dichloromethane, and 2g of PEG-600 into the reactor, stir and cool to about 0°C, and slowly alternately add 120ml of 30% hydrogen peroxide and 180g of 46% industrial Hydrobromic acid solution, keep stirring at -5°C-5°C for reaction, drop it in about 8 hours, and then react for 1 hour. Stop stirring, and after standing for 30 minutes, separate the upper layer of waste water and discard it; the lower layer of oil is stirred with 10 ml of 5% sodium carbonate solution for 1 hour to wash and neutralize to obtain the oil of the lower layer with pH=6. The dichloromethane solvent was recovered by distillation, and finally about 215.3 g of a white or light red solid (ie 4-methyl-2-bromo-6-methoxyphenol) was obtained.

[0028]Alkylation reaction: In the reactor, add 215.3g of the sol...

Embodiment 3

[0031] Bromination reaction, alkylation reaction are identical with embodiment 1.

[0032] Methoxidation reaction: In a low-pressure reactor with a capacity of 1L, add 116g (0.5mol) 3,4-dimethoxy-5-bromo-toluene solid, 400ml methanol, 180ml DMF, 48g99% sodium methoxide to the alkylation reaction in sequence , 10g cuprous chloride, 2g PEG-600, filled with nitrogen to drive away the air. Under the protection of nitrogen, the reaction was stirred at 90° C. for 4 hours. Then methanol and DMF were distilled off under normal pressure, cooled to normal temperature, and the reactant was repeatedly washed with 100ml×3 water to obtain a crude oil of 3,4,5-trimethoxytoluene, which was neutral and distilled under reduced pressure. Fractions at 116-118°C / 667Pa were collected to obtain 79g of the target compound with a chromatographic content of 99.5% and a melting point of 25°C.

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Abstract

The invention provides a method for preparing 3,4,5-triethoxy methylbenzene. The method comprises the following steps: carrying out bromination and hydrocarbonylation on 4-methyl guaiacol which is separated and extracted from bio-oil and used as a raw material, and further carrying out methoxidation to obtain 3,4,5-triethoxy methylbenzene. The method provided by the invention is simple and convenient in process, low in requirement on reaction equipment and reaction condition and short in reaction period. As the natural compound 4-methyl guaiacol extracted from biomass pyrolytic tar is taken as the raw material, the method is relatively low in cost and wide in resource, and a novel way is provided for deep processing and utilization of bio-oil.

Description

technical field [0001] The invention belongs to the technical field of biomass utilization, and in particular relates to a method for preparing 3,4,5-trimethoxytoluene. Background technique [0002] 3,4,5-Trimethoxytoluene, English name 3,4,5-Trimethoxytoluene, molecular formula C 10 h 14 o 3 , with a relative molecular mass of 182.22, having the structure shown in formula (1): [0003] [0004] (1) [0005] 3,4,5-Trimethoxytoluene is an important pharmaceutical intermediate for the synthesis of ubiquinone compounds such as idebenone and coenzyme Q. The methods for synthesizing 3,4,5-trimethoxytoluene reported in the current literature are as follows: (1) Using p-cresol as raw material, sulfonation reaction occurs under the action of oleum to prepare 2,6-disulfonic acid group -4-methylphenol, and then undergo alkali fusion, and react with dimethyl sulfate to synthesize 3,4,5-trimethoxytoluene. This method needs to consume a large amount of acid and alkali, which seri...

Claims

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Application Information

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IPC IPC(8): C07C43/205C07C41/16
CPCC07C41/16C07C41/22C07C43/2055C07C43/225C07C43/23
Inventor 朱锡锋朱昌朋李凯
Owner UNIV OF SCI & TECH OF CHINA
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