Method for synthesizing 4-n-butylresorcinol by microchannel reaction

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 hidden safety hazards and increased difficulty, save equipment space and reduce waste acid and residue , the effect of improving the reaction yield and purity

Active Publication Date: 2019-11-29
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

In addition, in the traditional reactor reaction, the reaction is exothermic and produces a large amount of gas when adding materials, which poses a great safety hazard and increases the difficulty of process scale-up.

Method used

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  • Method for synthesizing 4-n-butylresorcinol by microchannel reaction
  • Method for synthesizing 4-n-butylresorcinol by microchannel reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Weigh 100g of 4-n-butyryl resorcinol and dissolve it in toluene, cool it in ice to 0°C, then slowly add 32g (1.5eq) 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

[0039] 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 12 hours 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

[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 21g (1eq) of sodium borohydride in batches, and react at room temperature for 12 hours 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 by a microchannel reaction, belonging to the technical field of synthesis of cosmetic intermediates. The method comprises the following steps: dissolving 4-n-butyrylresorcinol in an organic solvent, adding a sodium borohydride reducing agent, and carrying out a reaction at room temperature; then feeding a reaction product into apreheating module, preheating the reaction product to 60-90 DEG C and using the preheated reaction product as a material 1; preheating a Raney nickel / organic solvent turbid liquid in the preheating module to 60-90 DEG C and using the preheated Raney nickel / organic solvent turbid liquid as a material 2; and feeding the two materials to a reaction module for a reaction so as to obtain 4-n-butylresorcinol. The method of the invention has the following advantages: the catalyst used in the method is low in cost; reaction conditions are mild; hydrogen can be slowly released for reduction; operationis relatively simple and safe; and 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 can inhibit 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...

Claims

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Application Information

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Patent Type & Authority Applications(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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