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Method for preparing hinokitiol

A technology of asphalt alcohol and ethanol, which is applied in the field of industrialization and high-purity preparation, can solve the problems of strict equipment process requirements, high price, and easy formation of dimers, so as to avoid isomers and solve safety problems Problems and the effect of eliminating potential safety hazards

Active Publication Date: 2019-01-04
INST OF ENVIRONMENT & SUSTAINABLE DEV IN AGRI CHINESE ACADEMY OF AGRI SCI +3
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because the reagents such as Grignard, dialkylaluminum hydride, and alkyllithium used in these methods are expensive, and in the process of gradually heating up by low temperature control, the equipment process requirements for gas phase conditions are strict; Alkyl body, resulting in low monoalkyl body yield, and the equilibrium composition of the product is basically an isomeric mixture of 1-isopropyl cyclopentadiene and 2-isopropyl cyclopentadiene, which is not suitable for the preparation of high Pure cypressenol
In addition, the raw material cyclopentadiene belongs to energetic compounds (rocket propellant), and its boiling point is low. explode
This causes the preparation of hinoki alcohol to be unable to carry out large-scale industrialization and application

Method used

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  • Method for preparing hinokitiol
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  • Method for preparing hinokitiol

Examples

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preparation example Construction

[0045] In the method for preparing cypress alcohol of the present invention, the preparation of compound 1 comprises the following steps:

[0046] The cyclohexene is mixed with bromomethane, and an addition reaction is carried out under the catalysis of triethylphenylammonium chloride and an inorganic base, the reaction temperature is -20 DEG C to 30 DEG C, and the reaction time is 0.5 to 30 hours; The volume ratio of hexene to tribromomethane is 1:0.5 to 1:100, preferably 1:2 to 1:10, and the volume ratio of cyclohexene to triethylphenylammonium chloride is 1000:1 to 10:1 , preferably 100:1 to 50:1; the inorganic base includes any one of sodium hydroxide and potassium hydroxide;

[0047] After the reaction was completed, it was quenched with hydrochloric acid, and the concentration of hydrochloric acid was 1M-10M; then, it was extracted and separated with dichloromethane, and compound 1 was collected from the dichloromethane solution, and the yield was 73%.

[0048] The gene...

Embodiment 1

[0049] Example 1 Synthetic preparation of compound 1

[0050] Dissolve 10 ml of cyclohexene in 50 ml of tribromomethane, add 0.1 g of triethylphenylammonium chloride (phase transfer catalyst), and cool the above solution to 0°C; after rapid stirring, add dropwise 24 g of 50% hydrogen Aqueous sodium oxide solution (nucleophilic reaction catalyst) was stirred at 0 °C for 2 hours, and then continued to stir at room temperature for 22 hours; then cooled to 0 °C, and 30 ml of 6M hydrochloric acid was added dropwise; the organic phase was separated, and the residual residue in the aqueous phase Compound 1 was extracted with dichloromethane; the organic phase was dried over anhydrous magnesium sulfate to remove desiccant and solvent; a colorless liquid compound 1 was obtained by distillation under reduced pressure with a yield of 73%.

[0051] The structure of compound 1 was characterized by hydrogen nuclear magnetic resonance spectroscopy (HNMR) and mass spectrometry (ESI-MS). The r...

Embodiment 2

[0057] Example 2 Synthetic preparation of compound 2

[0058] 7.6 g of compound 1 was added to 200 ml of a solution of chromium trioxide (30 g) in ether at 0 °C, and stirred at 25-30 °C for 1 hour, the reaction was poured into 1 liter of water, the organic phase was separated, and the water The compound 2 remaining in the phase was extracted with ether; the separated organic phase and the extract were mixed, and washed with sodium carbonate aqueous solution and saturated brine to remove the impurities remaining in the organic phase; after drying with anhydrous magnesium sulfate, distilled off ether to give compound 2 (6.8 g, 90% yield).

[0059] The structure of compound 2 was characterized by hydrogen nuclear magnetic resonance spectroscopy and mass spectrometry, and the relevant data are as follows:

[0060] 1 H NMR (CDCl 3 , 300MHz), δ: 4.32 (t, 1H), 4.08 (d, 1H), 3.91 (m, 1H), 2.42 (m, 2H), 1.96 (m, 2H); ESI-MS: 343 (M + ).

[0061] In the method for preparing cypress...

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Abstract

The invention discloses a method for preparing hinokitiol. The method includes the steps of conducting an addition reaction on bromoform and an initial raw material compound, namely cyclohexene, to obtain a first compound, namely 7,7-dibromo bicyclo[4.1.0]heptane; the first compound is subjected to an oxidization reaction to obtain a second compound, namely 3,7,7-tribromo bicyclo[4.1.0]heptyl-2-ketone; the second compound is subjected to a substitution reaction to obtain a third compound, namely 7,7-dibromo-3-hydroxy bicyclo[4.1.0] heptyl-3-alkene-2-ketone; the third compound is subjected to aring enlargement reaction to obtain a fourth compound, namely 4-bromo-2-hydroxy cycloheptyl-2,4,6-triene-1-ketone; the fourth compound is subjected to an alkylation reaction to obtain hinokitiol.

Description

technical field [0001] The invention relates to the technical field of preparation of cypress alcohol, in particular to the industrialization and high-purity preparation method of cypress alcohol. Background technique [0002] Hinokitiol, also known as Hinokitiol or Hinokitiol (β-Thujaplicin), is a natural compound of monoterpene with a seven-ring tropolone skeleton extracted from Chinese Taiwan cypress and Japanese Aomori cypress. Tropolone compounds have good broad-spectrum antibacterial properties, moisture retention and pest repelling effects, are high-safety plant components, and can be used as raw materials for the preparation of antibacterial and insect repellents. As the main component of Taiwanese cypress essential oil, it has a wide range of biological activities and strong bactericidal ability. For general bacteria, its minimum inhibitory concentration is 10-100ppm, and it has a fragrant smell and good effect. It can not only kill bacteria in the air , mold, and ...

Claims

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Application Information

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IPC IPC(8): C07C49/573C07C45/64C07C45/67C07C45/68C07C17/32C07C23/28C07C45/28C07C49/477
CPCC07C17/32C07C45/28C07C45/64C07C45/67C07C45/68C07C23/28C07C49/477C07C49/573
Inventor 刘家磊宋吉青何文清刘琪白文波
Owner INST OF ENVIRONMENT & SUSTAINABLE DEV IN AGRI CHINESE ACADEMY OF AGRI SCI
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