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A kind of method that microchannel reaction synthesizes 4-n-butylresorcinol

A technology of n-butyl resorcinol and n-butyryl resorcinol, which is applied in the field of cosmetic intermediate synthesis, can solve problems such as increased difficulty and potential safety hazards, reduce waste acid and residue, and save equipment space , the effect of simple operation

Active Publication Date: 2022-04-12
上海昕凯医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The two methods mentioned above are the conventional methods reported so far, and there are obvious defects in the scale-up of the process.
In addition, in the traditional reactor reaction, the reaction is exothermic and produces a large amount of gas when adding materials, which has great safety hazards and increases the difficulty of process scale-up.

Method used

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  • A kind of method that microchannel reaction synthesizes 4-n-butylresorcinol
  • A kind of method that microchannel reaction synthesizes 4-n-butylresorcinol
  • A kind of method that microchannel reaction synthesizes 4-n-butylresorcinol

Examples

Experimental program
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Effect test

Embodiment 1

[0039] Weigh 100g of 4-n-butyryl resorcinol and dissolve it in toluene, put it in an ice bath to 0°C, then slowly add 32g (1.5eq) of sodium borohydride in batches, and react at room temperature for 12 hours after the addition; then pour it into the pre- Heat module 1, preheat to 80°C; mix 67g of Raney nickel and isopropanol into preheat block 2, and preheat to 80°C. Then add the above two preheated materials into the reaction module, and the residence time is controlled at 200s. Collect the reaction solution flowing out, pour into ice water to quench, filter off the solid, evaporate most of the toluene, add 330mL of dichloromethane for extraction, evaporate the dichloromethane to dryness, and obtain 82g of white solid 4-n-butylresorcinol, Yield 89%, HPLC purity 99.3%.

Embodiment 2

[0041] Weigh 100g of 4-n-butyryl resorcinol and dissolve it in isopropanol, put it in an ice bath to 0°C, then slowly add 32g (1.5eq) of sodium borohydride in batches, and react at room temperature for 12h after the addition; Inject into preheating module 1 and preheat to 80°C; mix 67g of Raney nickel and isopropanol into preheating module 2 and preheat to 80°C. Then add the above two preheated materials into the reaction module, and the residence time is controlled at 200s. Collect the reaction solution flowing out, pour it into ice water to quench, filter off the solid, distill off the excess isopropanol, add 350 mL of dichloromethane for extraction, evaporate the dichloromethane to dryness, and obtain 89 g of white solid 4-n-butylresorcinol , yield 96%, HPLC purity 99.6%.

Embodiment 3

[0043] Weigh 100g of 4-n-butyryl resorcinol and dissolve it in isopropanol, put it in an ice bath to 0°C, then slowly add 21g (1eq) of sodium borohydride in batches, and react at room temperature for 12h after the addition; then pour it into Preheat module 1, preheat to 80°C; mix 67g of Raney nickel and isopropanol into preheat module 2, and preheat to 80°C. Then add the above two preheated materials into the reaction module, and the residence time is controlled at 200s. Collect the reaction solution flowing out, pour it into ice water to quench, filter off the solid, evaporate the excess isopropanol, add 350 mL of dichloromethane for extraction, evaporate the dichloromethane to dryness, and obtain 84 g of white solid 4-n-butylresorcinol , yield 91%, HPLC purity 99.5%.

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Abstract

The invention discloses a method for synthesizing 4-n-butylresorcinol through a microchannel reaction, and belongs to the technical field of cosmetic intermediate synthesis. The method is: dissolve 4-n-butyryl resorcinol in an organic solvent, add sodium borohydride reducing agent, and react at room temperature; then add it to the preheating module, and preheat it to 60-90°C as Material 1 and Raney nickel / organic solvent turbid liquid are also preheated in the preheating module to 60-90°C as material 2, and the two are added to the reaction module for reaction to obtain 4-n-butylresorcinol. The catalyst used in the method provided by the invention has low cost, mild reaction conditions, slow release of hydrogen for reduction, relatively simple operation and high safety, and the yield is as high as 96%.

Description

technical field [0001] The invention relates to the synthesis of resorcinol compounds, in particular to a method for synthesizing 4-n-butylresorcinol by microchannel reaction, and belongs to the technical field of cosmetic intermediate synthesis. Background technique [0002] 4-n-Butylresorcinol, also known as Rucinol, is an active ingredient in various cosmetics, which can inhibit the production of melanin. Its molecular structure is as follows: [0003] [0004] Specifically, it inhibits two enzymes necessary for melanin production, namely tyrosinase and 5,6-dihydroxyindole-2-carboxylate-oxidase. [0005] The method of synthesizing 4-n-butyl resorcinol mainly contains following two kinds at present: [0006] Method 1: use palladium carbon in methanol solvent to reduce 4-butyryl resorcinol by catalytic hydrogenation. Catalytic hydrogenation is a typical gas-liquid-solid three-phase heterogeneous reaction. In order to ensure the full contact of the three phases, high te...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C37/00C07C39/08B01J19/00
CPCC07C37/002B01J19/0093C07C39/08
Inventor 谭新刚张宗华孙欣怡
Owner 上海昕凯医药科技有限公司
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