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A kind of preparation method of m-methoxyphenol

A technology of methoxyphenol and resorcinol, which is applied in the field of preparation of chemical intermediates, can solve the problems of large catalyst consumption, high reaction consumption and energy consumption, inconvenient loading, etc., and achieves suitable mass production, reduces reaction conditions, The effect of simplifying the process flow

Active Publication Date: 2019-06-11
ZHEJIANG DINGLONG TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the patented catalyst needs to be prepared at high temperature, and it is inconvenient to load, and there are many considerations in industrial production; when performing etherification, it needs to be carried out under gas phase conditions, and a molten salt bath at 380 ° C is maintained, and the conversion rate of m-diphenol is low. , only 82.3%; the amount of catalyst is large, the reaction consumes high energy consumption, which results in high production cost, and it is difficult to realize industrial production

Method used

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  • A kind of preparation method of m-methoxyphenol

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Experimental program
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Effect test

Embodiment 1

[0022] The synthetic route of the present invention is as follows:

[0023]

[0024] Add 110g (1.0mol) of resorcinol, 5.0g (0.015mol) of tetrabutylammonium bromide, 500ml of toluene, and 100ml of water into a 1L four-necked flask, stir until the solids are completely dissolved, and start to drop NaOH solution (40g / 200ml), after dropping, cool down to 20°C, add Me dropwise 2 SO 4 151g (1.20mol), dripping complete insulation reaction, stop reaction when resorcinol2 SO 4 Adjust to strong acidity (pH 1-2), separate liquid, extract the water layer once with 250ml toluene, combine the organic phase, wash the organic phase twice with 250ml water, collect the organic phase, adjust the pH of the organic phase to strong with 25% NaOH solution Alkaline (pH 12-13), stir for 0.5 hours, separate liquid, use 50% H 2 SO 4 Adjust the pH to strong acidity (pH is 1-2), add 200ml of toluene to extract after stirring, collect the organic phase, then extract the water layer with 100ml of t...

Embodiment 2

[0026] Add 110g of resorcinol, 5.0g of tetrabutylammonium bromide, 500ml of toluene, and 100ml of water into a 1L four-neck flask, stir until the solids are completely dissolved, then add an appropriate amount of NaOH solution (40g / 200ml) dropwise to make the system alkaline properties, followed by double dropwise addition of the remaining NaOH solution (40g / 200ml) and Me 2 SO 4 151g, drop and keep warm at 20°C for reaction, stop reaction when resorcinol 2 SO 4 Adjust the pH to 1-2, separate the liquids, extract the aqueous layer once with 250ml toluene, combine the organic phases, wash the organic phase twice with 250ml 0.1mol / L NaOH solution, collect the organic phase, adjust the organic phase with 200g 20% ​​NaOH solution pH to 12-13, stir for 0.5h, separate liquid, use 50% H 2 SO 4 Adjust the pH to 1-2, add 200ml of toluene after stirring for extraction, collect the organic phase, and recover the toluene in the product and by-products by rotary evaporation at 50°C to o...

Embodiment 3

[0028] Add 110g of resorcinol, 5.0g of tetrabutylammonium bromide, 500ml of ethyl acetate, and 100ml of water into a 1L four-necked flask, and stir until the solids are completely dissolved. Alkaline, then add the remaining NaOH solution (40g / 200ml) and Me 2 SO 4 151g, drop and keep warm at 20°C for reaction, stop reaction when resorcinol 2 SO 4 Adjust the pH to 1-2, separate the layers, extract the aqueous layer once with 250ml toluene, combine the organic phases, wash the organic phase twice with 250ml 0.1mol / L NaOH solution, collect the organic phase, adjust the organic phase with 200g 20% ​​NaOH solution pH to 12-13, stir for 0.5h, separate liquid, use 50% H 2 SO 4 Adjust the pH to 1-2, add 200ml of toluene to extract after stirring, collect the organic phase, and recover the toluene in the product and by-product by rotary evaporation at 50°C to obtain 115.6g of the target product with a yield of 93.2% and HPLC>96.2%.

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Abstract

The invention relates to a method for preparing methoxy phenol, and the method comprises the following steps: (1) dissolving resorcinol and a phase transfer catalyst in a certain solvent, adding an alkali liquid, dropwise adding a methylating agent under alkaline conditions, after the methylating agent is completely added dropwise, thermally insulating for reaction, and when the resorcinol is less than 5%, stopping the reaction; 2) adjusting the pH of the reaction liquid to strongly-acid, separating the liquid, using a certain amount of toluene for extraction of a water layer, merging organic phase, washing the organic phases with water and a dilute lye, then collecting the organic phase, adjusting the pH of the collected organic phase with an alkali liquid to strongly-alkaline, stirring for a period of time, separating the liquid, using an acid to adjust the pH of a water phase to strongly-acid, stirring, adding the toluene for extraction, collecting an organic phase, using the toluene for extraction of a water layer, merging organic phases, performing rotary evaporation at certain temperature for recovery of the toluene in a product and by-products to obtain a product with HPLC greater than 95.0 %. The method improves the purity of the product, simplifies the process flow, reduces reaction conditions, and makes the product more suitable for mass production.

Description

technical field [0001] The invention relates to a preparation method of a chemical intermediate, in particular to a preparation method of m-methoxyphenol. Background technique [0002] M-methoxyphenol is the monomethyl ether of resorcinol, and it is an important pharmaceutical and chemical raw material, which can be used in many fields such as plastic anti-oxidation and anti-aging agents, fungicides, and photosensitive materials. [0003] There are few domestic reports about the preparation method of m-methoxyphenol. Chinese patent CN 1157283 discloses a method for producing alkyl ethers of phenol from phenol and alcohol with higher selectivity and yield than the usual method. This patent The atomic ratio composition is Cs when there is no oxygen 1 Si 30 or Cs 1 Si 10 As a catalyst, a gas-phase etherification reaction is carried out in a stainless steel reaction tube by feeding a mixed gas composed of phenol / methanol / nitrogen at 380°C. The process, which is stable over ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C41/16C07C43/23
CPCC07C41/16C07C41/34C07C41/38C07C43/23
Inventor 潘志军张学金宁人许惠钢郭志超刘文峰刘琛
Owner ZHEJIANG DINGLONG TECH
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