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A kind of method for preparing hinoki alcohol

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

Active Publication Date: 2020-09-04
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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  • A kind of method for preparing hinoki alcohol
  • A kind of method for preparing hinoki alcohol
  • A kind of method for preparing hinoki alcohol

Examples

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preparation example Construction

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

[0046] Mix cyclohexene with tribromomethane and carry out addition reaction under the catalysis of triethylphenyl ammonium chloride and inorganic base, the reaction temperature is -20°C to 30°C, and the reaction time is 0.5 to 30 hours; wherein, cyclohexene 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, the concentration of hydrochloric acid was 1M-10M; then extracted and separated with dichloromethane, compound 1 was collected from the dichloromethane solution, and the yield was 73%.

[0048] The general reaction formul...

Embodiment 1

[0049] The synthetic preparation of embodiment 1 compound 1

[0050] Dissolve 10 milliliters of cyclohexene in 50 milliliters of tribromomethane, add 0.1 grams of triethylphenylammonium chloride (phase transfer catalyst), and cool the above solution to 0° C.; add 24 grams of 50% hydrogen dropwise after rapid stirring Sodium oxide aqueous solution (nucleophilic reaction catalyst), stirred at 0°C for 2 hours, 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 remaining 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 vacuum distillation with a yield of 73%.

[0051] The structure of compound 1 was characterized by hydrogen nuclear magnetic resonance (HNMR) and mass spectrometry (ESI-MS), and the relevant data are as follows:...

Embodiment 2

[0057] The synthetic preparation of embodiment 2 compound 2

[0058] 7.6 grams of compound 1 were added to 200 milliliters of chromium trioxide (30 grams) in diethyl ether solution at 0° C., and stirred for 1 hour at 25-30° C., the reactant 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 aqueous sodium carbonate solution and saturated brine to remove the remaining impurities in the organic phase; after drying with anhydrous magnesium sulfate, distilled off diethyl ether to obtain compound 2 (6.8 g, yield 90%).

[0059] The structure of compound 2 was characterized by proton nuclear magnetic resonance 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 fo...

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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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Patent Type & Authority Patents(China)
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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