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Preparation method of 5,6-epoxy-5,6-dihydro-beta-ionol

A technology of ionol and ionone, applied in 5 fields, can solve problems such as compound instability and easy polymerization

Inactive Publication Date: 2010-07-28
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above three compounds are widely used in tobacco, but because these compounds are unstable and easy to polymerize

Method used

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  • Preparation method of 5,6-epoxy-5,6-dihydro-beta-ionol

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Experimental program
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Embodiment 1

[0020] At room temperature, 5,6-epoxy-5,6-dihydro-β-ionone 0.563g (97.10%, 2.63mmol) was dissolved in 9.21ml of anhydrous methanol, and 0.984g of cerium chloride heptahydrate was added ( 2.63mmol) was stirred until dissolved, then slowly added 0.10g (2.63mmol) of sodium borohydride within 5 minutes, continued to stir for 5 minutes after the addition was complete, and ended the reaction, and adjusted the pH to neutral with 5% dilute hydrochloric acid. Extract with ether, filter with a glass funnel, combine the filtrates, anhydrous MgSO 4 Let dry overnight. After filtration, the solvent was distilled off to obtain 0.54 g of the product with a GC content of 93.86% and a yield of 91.84%. After separation by silica gel column, the mixed solvent of petroleum ether and ethyl acetate was used as eluent, the volume ratio was 10:1, and the solvent was evaporated to obtain colorless 5,6-epoxy-5,6-dihydro-β- Ionol, the purity is greater than 98.00%.

[0021] Infrared spectral data:

...

Embodiment 2

[0029] Under ice-water bath, dissolve 0.835g (97.10%, 3.90mmol) of 5,6-epoxy-5,6-dihydro-β-ionone in 5.85ml of anhydrous methanol, and add 0.967g of anhydrous cerium chloride (3.90mmol) was stirred until dissolved, then slowly added 0.148g (3.90mmol) of sodium borohydride within 5 minutes, continued to stir for 5 minutes, ended the reaction, and adjusted the pH to neutral with 5% dilute hydrochloric acid by mass fraction. Extract with ether, filter with a glass funnel, combine the filtrates, anhydrous MgSO 4 Let dry overnight. The next day, it was filtered and the solvent was distilled off to obtain 0.78 g of the product with a GC content of 92.15% and a yield of 87.80%. After separation by silica gel column, the mixed solvent of petroleum ether and ethyl acetate with a volume ratio of 10:1 was used as eluent to rinse, and the colorless 5,6-epoxy-5,6-dihydro- β-ionol, the purity is 98.00%.

Embodiment 3

[0031] _____Under an ice-water bath, dissolve 1.092g (97.10%, 5.10mmol) of 5,6-epoxy-5,6-dihydro-β-ionone in 22.95ml of anhydrous methanol, and add anhydrous cerium chloride After stirring 1.265g (5.10mmol) until dissolved, slowly add 0.194g (5.10mmol) of sodium borohydride within 5 minutes, continue stirring for 5 minutes to end the reaction, and adjust the pH to neutral with 5% dilute hydrochloric acid. Extract with ether, filter with a glass funnel, and use anhydrous MgSO 4 Let dry overnight. The next day, it was filtered and the solvent was distilled off to obtain 1.04 g of the product with a GC content of 93.18% and a yield of 90.53%. Separation on a silica gel column, eluting with a mixed solvent of petroleum ether and ethyl acetate as eluent, the volume ratio is 10:1, and the colorless 5,6-epoxy-5,6-dihydro- β-ionol, 97.95% pure.

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Abstract

The invention provides a preparation method of 5,6-epoxy-5,6-dihydro-beta-ionol, comprising the following steps of: selectively reducing carbonyl in 5,6-epoxy-5,6-dihydro-beta-irisone used as raw material by using NaBH4 and CeCl3.7H2O, and synthesizing to obtain the 5,6-epoxy-5,6-dihydro-beta-ionol, wherein the yield reaches 87.8-91.84 percent. The purity is higher than 95.00 percent by silicagel column separation. Compared with a preparation method reported in the literature of carrying out the epoxidation reaction of beta-ionol by using m-chlorobenzene performic acid in sodium bicarbonate and methylene dichloride at room temperature to obtain the 5,6-epoxy-5,6-dihydro-beta-ionol, the reaction time is greatly shortened, and the yield is obviously increased.

Description

technical field [0001] The present invention relates to a preparation method of aromatic terpene alcohol, in particular to a preparation method of 5,6-epoxy-5,6-dihydro-β-ionol. Background technique [0002] 5,6-epoxy-5,6-dihydro-β-ionol is a C 13 -Norprene derivatives, which are metabolic degradation products of homoterpenoids. It is a very useful spice and pharmaceutical intermediate, especially in the spice, food and tobacco industries, and has a wide range of applications. In 1972, E.Demole et al. discovered an important component of large pillar trienone (1) in Burley tobacco, Turkish tobacco and Greek tobacco leaves. Afterwards, Swedish chemists discovered a compound of similar structure 3-oxo- α-ionol (2) and later 5,8-macrodien-4-one (3) were found in Virginia tobacco leaves. The above three compounds are widely used in tobacco, but because these compounds are unstable, they are easy to polymerize. Various carbonates and glycoside derivatives made into (2) by BAS...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D303/14C07D301/00
Inventor 杨始刚嵇金丽黄红
Owner SHANGHAI INST OF TECH
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