Method for preparing 1,8-cineole derivative from 3-carene

A technology for eucalyptol and derivatives, which is applied in the field of preparing 1,8-cineole derivatives from 3-carene, can solve the problems of rare amine derivatives, and achieve abundant natural reserves, low price and high yield selective effect

Active Publication Date: 2021-11-05
INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Compared with hydroxyl and halogen, reports on amine derivatives of 1,8-cineole are even rarer

Method used

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  • Method for preparing 1,8-cineole derivative from 3-carene
  • Method for preparing 1,8-cineole derivative from 3-carene
  • Method for preparing 1,8-cineole derivative from 3-carene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Example 1 Preparation of product A with 3-hydroxy-4-bromo-carbene as main component

[0041] 10.8g 3-carene, 8g CaCO 3 , 40 mL of water, 80 mL of 1,4-dioxane and 20 g of NBS were sequentially added to the reaction flask, and stirred at room temperature for 2 h; the reaction solution was transferred to 200 mL of water, filtered to remove the precipitate, and extracted with ethyl acetate (200 mL × 3 times), The aqueous layer was discarded; the organic layer was washed with 10% sodium thiosulfate-aqueous solution (200 mL×3 times), the aqueous layer was discarded, and the organic layer was dried by adding anhydrous sodium sulfate; the desiccant was removed by filtration, and the solvent was recovered by rotary evaporation to obtain the product A15.2g, wherein the GC content of compound II is 71.8%.

Embodiment 2

[0042] Example 2 Preparation of 2-bromo-1,8-cineole

[0043] Add 1 g of product A obtained in Example 1 and 5 mL of chloroform into the reaction flask, turn on and stir, add 0.94 g of trimethylbromosilane, and stir at 20°C for 1 h; the solvent is recovered by rotary evaporation to obtain product B, wherein compound III, The GC contents of compound VI and compound VII are: 42.95%, 16.18% and 13.14%, respectively.

Embodiment 3

[0044] Example 3 Preparation of 2-bromo-1,8-cineole

[0045] Add 1 g of product A obtained in Example 1 and 5 mL of chloroform into the reaction flask, turn on and stir, add 0.47 g of trimethylbromosilane, and stir at 20°C for 1 h; the solvent is recovered by rotary evaporation to obtain product B, wherein compound III, The GC contents of compound VI and compound VII are: 36.61%, 14.68% and 6.53%, respectively.

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Abstract

The invention discloses a method for preparing a 1,8-cineole derivative from 3-carene, which comprises the following steps: reacting 3-carene with N-bromosuccinimide at room temperature to generate a product A with 3-hydroxy-4-bromo-carane as a main component; reacting the product A under the action of trimethylbromosilane and the like to generate a product B, and conducting separating and purifying to obtain 2-bromo-1,8-cineole; then conducting reacting with ammonia water to generate a mixture of 2-hydroxy-1,8-cineole and 2-amino-1,8-cineole; adding HCl to convert the 2-amino-1,8-cineole into ammonia salt, separating out the ammonia salt in an organic solvent, and separating the ammonia salt from the 2-hydroxy-1,8-cineole; and dissolving the solid ammonia salt in water, adding alkali to convert the ammonia salt into amine again, and extracting and recycling the amine through an organic solvent. The conversion rate of all reaction raw materials is close to 100%, and the total selectivity of 2-hydroxy-1,8-cineole and 2-amino-1,8-cineole is greater than 98%.

Description

technical field [0001] The invention relates to a method for preparing 1,8-cineole derivatives from 3-carene, in particular to a method for simultaneously preparing 1,8-cineole containing three different groups of halogen, hydroxyl and amino groups. Derivative method. Background technique [0002] 1,8-Cineole is an important oxygen-containing monoterpene compound with outstanding activities such as antibacterial, anti-inflammatory, insecticidal, antioxidant, etc. It is widely used in food, daily chemicals, medicine and other industries (Chinese modern pharmaceutical impurities, 2014, 16(4):97-100). Derivatives of cineole have also been shown to have a wide range of biological activities. Barton et al. first synthesized 3-hydroxy-1,8-cineole, and then prepared a series of 1,8-cineole esters on this basis. Derivatives, and their herbicidal activities were determined, the results showed that these compounds are effective post-emergent herbicides for ryegrass and radishes (Jou...

Claims

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Application Information

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IPC IPC(8): C07D493/08C07C29/62C07C29/00C07C35/48
CPCC07D493/08C07C29/62C07C29/00C07C2601/14C07C2601/16C07C35/48
Inventor 王婧赵振东陈玉湘徐士超卢言菊古研毕良武程贤
Owner INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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