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Synthesis method of 4-isopropylresorcinol

A technology of propyl resorcinol and its synthesis method, which is applied in chemical instruments and methods, preparation of organic compounds, production of bulk chemicals, etc., can solve problems such as complex product composition and difficult purification, shorten hydrogenation time, The effect of reducing temperature and pressure

Active Publication Date: 2018-01-09
济南美高生物医药科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The second method is the Friedel-Crafts alkylation of resorcinol and isopropanol in the presence of a Lewis acid, but the composition of the product obtained by this synthetic method is relatively complex and difficult to purify

Method used

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  • Synthesis method of 4-isopropylresorcinol
  • Synthesis method of 4-isopropylresorcinol

Examples

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preparation example Construction

[0020] Such as figure 1 Shown, a kind of synthetic method of 4-isopropyl resorcinol comprises the steps:

[0021] S1, group protection: in the presence of solvent and potassium carbonate, 2,4-dihydroxyacetophenone and halomethyl ether react to generate 2,4-dioxymethoxyacetophenone;

[0022] S2, Grignard reaction: 2,4-dioxymethoxyacetophenone reacts with Grignard reagent to prepare 2,4-dioxymethoxyphenylpropanol;

[0023] S3. Hydrodeoxygenation: 2,4-dioxymethoxyphenylpropanol is subjected to a hydrogenation reaction in the presence of a hydrogenation catalyst to obtain 2,4-dioxymethoxycumene;

[0024] S4. Deprotection: 2,4-dioxymethoxycumene is deprotected in the presence of a solvent and concentrated hydrochloric acid to obtain 4-isopropylresorcinol.

[0025] In S1, the solvent is N,N-dimethylformamide, and the halomethyl ether is chloromethyl ether.

[0026] In S1, add 2,4-dihydroxyacetophenone to N,N-dimethylformamide, then add anhydrous potassium carbonate and chlorometh...

specific Embodiment 1

[0031] S1: Add 100 grams of 2,4-dihydroxyacetophenone to 1 liter of N,N-dimethylformamide, add 200 grams of anhydrous potassium carbonate, then add 115 grams of chloromethyl methyl ether, and react at 60 degrees After 8 hours, cool and filter, add 3 L of water to separate the liquid, then extract the water phase with ethyl acetate three times and combine it with the organic phase, dry and evaporate the solvent to obtain 150 g of the product;

[0032] S2: Add 150 grams of the product obtained in S1 into 2 liters of anhydrous tetrahydrofuran, cool to 0°C, add 250 ml of 3M methylmagnesium chloride dropwise, then react at 0°C for 2 hours, add 1 liter of saturated ammonium chloride aqueous solution to quench The water layer obtained after the liquid separation was extracted 3 times with ethyl acetate, then combined in the organic phase, dried, and evaporated to remove the solvent to obtain 144 grams of the product;

[0033] S3: Add 144 grams of the product obtained in S2 to 1 liter...

specific Embodiment 2

[0035] S1: Add 100 grams of 2,4-dihydroxyacetophenone to 1 liter of N,N-dimethylformamide, add 200 grams of anhydrous potassium carbonate, then add 115 grams of chloromethyl methyl ether, and react at 50 degrees After 10 hours, cool and filter, add 3L of water to separate the liquid, then extract the water phase with ethyl acetate 4 times and combine it with the organic phase, dry and evaporate the solvent to obtain 148 g of the product;

[0036] S2: Add 148 grams of the product obtained in S1 to 2 liters of anhydrous tetrahydrofuran, cool to 0°C, add 250 ml of 3M methylmagnesium bromide dropwise, then react at 0°C for 2 hours, add 1 liter of saturated ammonium chloride The aqueous solution was quenched, and the aqueous layer obtained after the separation was extracted 3 times with ethyl acetate, then combined in the organic phase, dried, and evaporated to remove the solvent to obtain 140 grams of the product;

[0037] S3: Add 140 grams of the product obtained in S2 to 1 liter...

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Abstract

The invention discloses a synthesis method of 4-isopropylresorcinol. The method comprises the following steps: group protection, Grignard reaction, hydrodeoxygenation and deprotection. According to the method, a novel protecting group halomethyl methyl ether is adopted for protecting phenolic hydroxy, then the Grignard reaction is performed on 3 milliliters of methylmagnesium chloride or methylmagnesium bromide, hydrogenation is performed under low pressure and normal temperature in the presence of acid, and the protecting group is removed with hydrochloric acid to obtain the 4-isopropylresorcinol. The problem of difficulty in treatment after Witting reaction is solved, the temperature and the pressure of hydrogenation reaction are reduced, the hydrogenation time is shortened, deprotectionis finally implemented under a mild condition, and the whole process is a safe production process capable of implementing industrial production.

Description

Technical field: [0001] The present invention relates to a kind of synthetic method of 4-isopropyl resorcinol. Background technique: [0002] 4-Isopropyl resorcinol is an important fine chemical intermediate, and the current main synthesis methods can be classified into the following two types: [0003] The first method is to protect 2,4-dihydroxyacetophenone with benzyl bromide or benzyl chloride, then use Witting reaction, and then carry out hydrogenation to obtain the final product. Due to the influence of the objective synthesis mechanism, the Witting reaction will produce a large amount of waste triphenylphosphine that is difficult to handle, and high temperature and high pressure are required in the hydrogenation process, and the hydrogenation reaction speed is relatively slow. Generally, it takes more than 20 hours to complete the reaction, reaching a relative Ideal yield. The second method is the Friedel-Crafts alkylation of resorcinol and isopropanol in the presen...

Claims

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Application Information

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IPC IPC(8): C07C37/055C07C39/08
CPCY02P20/55
Inventor 肖童董月辉陈茂营寇增杰
Owner 济南美高生物医药科技有限公司
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