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Method for synthesizing 3-(4-methyl benzene methylene) camphor

A technology of methylbenzylidene and p-methylbenzaldehyde, applied in the field of 3-camphor synthesis, can solve the problems of complicated process, inconvenient operation, etc., and achieve the effects of less waste liquid and easy recovery

Inactive Publication Date: 2016-10-05
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are few reports about 3-(4-methylbenzylidene) camphor synthesis at present, and only people such as Takao Saito report in Archive for Organic Chemistry, 2004 (ii): 152-171 and adopt potassium tert-butoxide as catalyst Synthetic 3-(4-methylbenzylidene) camphor, but the method is complex and inconvenient to operate

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] 4.56 g camphor, 0.948 g supported catalyst KOH / Al 2 o 3 1. Add 60 mL of tert-butanol to a four-neck flask equipped with a stirrer and a thermometer, heat to 78°C, and add 3.60 g of p-tolualdehyde dropwise at a rate not higher than 5 drops / second. React for 4 h. After the reaction finishes, filter and remove the loaded catalyst KOH / Al 2 o 3 , washed with saturated brine, dried over magnesium sulfate, and recovered the solvent under normal pressure. The product was obtained by recrystallization from ethanol aqueous solution and drying treatment, the yield was 56.8%, and the purity of 3-(4-methylbenzylidene) camphor was 99.50% according to gas chromatography.

Embodiment 2

[0020] 4.56 g camphor, 1.422 g supported catalyst KOH / Al 2 o 3 1. Add 60 mL of tert-butanol to a four-necked flask equipped with a stirrer and a thermometer, heat to 78°C, and slowly add 3.60 g of p-tolualdehyde dropwise at a rate not higher than 5 drops / second. React for 4 h. After the reaction finishes, filter and remove the loaded catalyst KOH / Al 2 o 3 , washed with saturated brine, dried over magnesium sulfate, and recovered the solvent under normal pressure. The product was obtained by recrystallization from ethanol aqueous solution and drying treatment, the yield was 76.8%, and the purity of 3-(4-methylbenzylidene) camphor by gas chromatography analysis was 99.48%.

Embodiment 3

[0022] 4.56 g camphor, 2.370 g supported catalyst KOH / Al 2 o 3 1. Add 60 mL of tert-butanol to a four-necked flask equipped with a stirrer and a thermometer, heat to 78°C, and slowly add 3.60 g of p-tolualdehyde dropwise at a rate not higher than 5 drops / second. React for 4 h. After the reaction finishes, filter and remove the loaded catalyst KOH / Al 2 o 3 , washed with saturated brine, dried over magnesium sulfate, and recovered the solvent under normal pressure. The product was obtained by recrystallization from ethanol aqueous solution and drying treatment, the yield was 80.0%, and the purity of 3-(4-methylbenzylidene) camphor was 99.50% according to gas chromatography analysis.

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PUM

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Abstract

The invention discloses a method for synthesizing 3-(4-methyl benzene methylene) camphor. The method comprises the following steps that firstly, camphor, a reaction solvent and an immobilized catalyst KOH / Al2O3 are added into a reaction container; secondly, the temperature is raised to a reaction temperature, and p-tolualdehyde is added dropwise; thirdly, after the reaction is finished, the immobilized catalyst KOH / Al2O3 is removed through filtration, washing is carried out through saturated brine, drying is carried out through magnesium sulfate, and the reaction solvent is recycled at normal pressure; fourthly, recrystallization is carried out through an ethanol solution, and by means of drying treatment, the product is obtained. The method for synthesizing the 3-(4-methyl benzene methylene) camphor through the immobilized catalyst KOH / Al2O3 in a catalyzing mode is simple and easy to implement, little liquid waste is caused, the catalyst is recycled easily, and the yield can reach 85%. The purity of the 3-(4-methyl benzene methylene) camphor prepared through the recrystallization post-treatment method can reach 99.5%.

Description

technical field [0001] The present invention relates to the synthesis of 3-(4-methylbenzylidene) camphor, specifically using supported catalyst KOH / Al 2 o 3 The method catalyzes the aldol condensation reaction of camphor and p-methylbenzaldehyde to obtain 3-(4-methylbenzylidene)camphor. Background technique [0002] With the strengthening of health awareness and the continuous improvement of people's material living standards, cosmetics have changed from a luxury of skin care to a necessity, and sunscreen cosmetics occupy an important position. Sunscreen cosmetics are not limited to summer use, they need sunscreen all year round. Sunscreen agents are added to sunscreen cosmetics to absorb the ultraviolet rays in the sun and protect human skin from sunburn by ultraviolet rays. Benzophenone-3, methoxy Ethylhexyl cinnamate, octocrylene (as acid), 3-(4-methylbenzylidene) camphor, etc. are commonly used sunscreen ingredients. [0003] 3-(4-Methylbenzylidene) camphor is a good ...

Claims

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Application Information

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IPC IPC(8): C07C45/74C07C49/683
CPCY02P20/584
Inventor 李斌栋苏莉莉
Owner NANJING UNIV OF SCI & TECH