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The production process of undecyloxyethanol, the aggregation pheromone of Monochamus alternatus

A technology of undecyloxyethanol and monochamus monochamus, which is applied in the field of production technology of monochamus alternatus aggregation pheromone undecyloxyethanol, can solve the problem of high price, only 47% yield and difficult product Extraction and other problems, to achieve the effect of simple and convenient operation, mild reaction conditions, and low production cost

Active Publication Date: 2020-09-25
SUZHOU HUADAO BIOLOGICAL PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] 2. In N,N-dimethylformamide, react a large equivalent of ethylene glycol with sodium hydrogen to produce sodium alkoxide, and then add 1-bromoundecane to react to prepare undecyloxyethanol[J. Chem.Ecol.2010,36,570-583]; the reaction also needs a high equivalent of ethylene glycol, and N,N-dimethylformamide is used as a solvent, making it more difficult for the product to be extracted from the reaction system, resulting in a yield of only 47 %
[0010] In the above two synthetic methods, 1-bromoundecane is used as the raw material for synthesis. The raw material is expensive (~￥5000 / 500g), and there is no bulk product available, which makes Monochamus alternatus gather information Large-scale production of undecyloxyethanol is difficult

Method used

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  • The production process of undecyloxyethanol, the aggregation pheromone of Monochamus alternatus
  • The production process of undecyloxyethanol, the aggregation pheromone of Monochamus alternatus
  • The production process of undecyloxyethanol, the aggregation pheromone of Monochamus alternatus

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Add 172 grams (1mol, 1eq.) of undecyl alcohol and 800 milliliters of toluene in the reaction flask, add 25.3 grams (1.1mol, 1.1eq.) of metal sodium in batches under heating and reflux, and reflux until the reaction of metal sodium is complete; add 8.3 grams ( 0.05mol, 0.05eq.) Potassium iodide, and then add 150.7 grams (1.1mol, 1.1eq.) 2-tert-butoxychloroethane dropwise. After the addition is complete, continue to heat and reflux the reaction. After gas phase detection, the reaction was completed, cooled, 200 ml of water was added to extract the reaction, the liquid was separated, and the organic phase was concentrated.

[0035] Add 800 ml of dichloromethane to the above residue, stir to dissolve, add 100 ml of trifluoroacetic acid, stir at 25°C until the reaction is complete, use saturated aqueous sodium carbonate solution to adjust the pH to 8, separate the layers, and use anhydrous sulfuric acid for the organic phase Dry over sodium, filter with suction, concentrate ...

Embodiment 2

[0037]Add 172 grams (1mol, 1eq.) of undecyl alcohol and 800 milliliters of tetrahydrofuran in the reaction flask, add 48 grams (1.2mol, 1.2eq., 60%) sodium hydrogen in batches, heat and reflux for 30 minutes; add 7.4 grams (0.02mol , 0.02eq.) tetrabutylammonium iodide, and then dropwise added 150.7 grams (1.1mol, 1.1eq.) 2-tert-butoxychloroethane, after the addition was complete, continue to heat and reflux the reaction. After gas phase detection, the reaction was completed, cooled, added 200 ml of water to extract the reaction, concentrated to remove the solvent, extracted with dichloromethane, combined the organic phases, and concentrated.

[0038] Add 300 milliliters of concentrated hydrochloric acid to the above residue, stir and react at 35°C; the gas phase detection reaction is completed, dichloromethane extraction, combined organic phase, sodium carbonate drying, suction filtration, filtrate concentration, vacuum distillation to obtain 184 grams of undecyl oxide Base et...

Embodiment 3

[0040] Add 688 grams (4mol, 1eq.) of undecanol, 52.8 grams (0.2mol, 0.05eq.) of octadecadecanol and 5 liters of tetrahydrofuran into the reaction flask, and add 538 grams (4.8mol, 1.2eq.) of tert-butyl in batches Potassium alkoxide was heated to reflux for 30 minutes; 657.6 grams (4.8mol, 1.2eq.) of 2-tert-butoxyethyl chloride was added dropwise, and the reaction was continued under reflux. After gas phase detection, the reaction was completed, cooled, added 500 ml of water to extract the reaction, concentrated to remove the solvent, extracted with dichloromethane, combined the organic phases, and concentrated.

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Abstract

The invention discloses a technology for producing Monochamus alternatus Hope aggregation pheromone undecyloxyethanol. The technology comprises the following steps: 1, carrying out a nucleophilic substitution reaction on a raw material 2-chloroethyl tert-butylether and undecanol in a first solvent containing a proper amount of a first catalyst under an alkaline condition at 0-120 DEG C to prepare1-(2-tert-butoxyethoxy)-undecane; and 2, carrying out a tert-butyl group removal reaction on the prepared 1-(2-tert-butoxyethoxy)-undecane in a second solvent containing a proper amount of a second catalyst under an acidic condition at 0-100 DEG C to obtain the target product undecyloxyethanol. The technology has the advantages of realization of the purity of the obtained target product being morethan 99%, mild reaction conditions, high yield, simplicity and convenience in operation, low production cost, and suitableness for amplified production.

Description

technical field [0001] The invention relates to the field of forest pest control, in particular to a production process of monochamus monochamus aggregation pheromone undecyloxyethanol. Background technique [0002] Pine wood nematode is a major worldwide forest disease, and its control has always been a worldwide problem. At present, no effective control technology has been found for pine trees infected with the disease. The disease has successively occurred in many provinces of my country, killing tens of millions of pine trees. The average annual loss caused by pine wood nematode is nearly 2 billion yuan, and the loss of ecological service value is as high as more than 6 billion yuan. Moreover, the disease spreads in my country at a rate of 75,000 mu per year. Pine wood nematode is a serious and dangerous quarantine pest, and pine xylophilus disease is a devastating disease of pine trees. Once a pine tree is infected, it cannot be cured, and the death rate is fast. It c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C41/26C07C43/13
CPCC07C41/16C07C41/26C07C43/13C07C43/046
Inventor 刘明荣陆军
Owner SUZHOU HUADAO BIOLOGICAL PHARMA
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