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Synthesis method of grapholitha molesta sex pheromone (Z/E)-8-dodecene acetate

The invention relates to a technology for the sex pheromone and synthesis method of the pear worm, which is applied in the field of chemical synthesis of the sex pheromone of Lepidoptera pests, can solve the problems of harsh operating conditions, high cost, easy explosion and the like, and achieves mild conditions and high yield. , the effect of fewer steps

Active Publication Date: 2014-12-03
SHANXI AGRI UNIV
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

[0011] Among them, route 1 and route 2 both involve the use of NaH dissolved in DMSO during the Wittig reaction to generate double bonds. This operation will generate a large amount of H in a short time. 2 , very prone to explosion, dangerous operation, and not suitable for industrial production; at the same time, the Wittig reaction of route two also needs to be carried out at a low temperature of -78°C, the operating conditions are harsh, and the cost is too high; When E)-dodecen-1-alcohol, the amount of NaH is halved, but a large amount of H will still be produced in the process of industrial production 2 , and its synthetic method is not suitable for industrial production

Method used

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  • Synthesis method of grapholitha molesta sex pheromone (Z/E)-8-dodecene acetate
  • Synthesis method of grapholitha molesta sex pheromone (Z/E)-8-dodecene acetate
  • Synthesis method of grapholitha molesta sex pheromone (Z/E)-8-dodecene acetate

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Experimental program
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Embodiment 1

[0031] a. 8-Bromo-1-octanol synthesis

[0032] 1,8-octanediol (1.46kg, 10mol) and toluene (25L) were added to the reactor, stirred and heated to 80-90°C, and 47% of pale yellow HBr (1.9Kg, 11mol) was added dropwise in four times. ), every half an hour, the mol ratio of four times of dropping HBr was 10:5:3:2, after the dropping was completed, the samples were incubated for 2 hours for sampling analysis; TLC monitoring, when 1,8-dibromooctane When the content reaches 3%, it is the end point of the reaction, cool to normal temperature, separate layers, wash the organic layer 3 times with 5% NaOH, 10% HCl, water, and saturated sodium bicarbonate solution in turn, until neutral, add Na 2 SO 4 Dry overnight. The solvent was removed with a rotary evaporator to obtain 1.78kg of 8-bromo-1-octanol, the yield of the product was 81%, and the content was >95% by GC inspection.

[0033] b. Synthesis of 8-hydroxyoctyl triphenylphosphine salt

[0034] Add 8-bromo-1-octanol (1.7kg, 8.1mol...

Embodiment 2

[0040] a. 8-Bromo-1-octanol synthesis

[0041] Add 1,8-octanediol (1.02kg, 7mol) and benzene (18L) to the reactor, stir and heat up to 80-90°C, slowly add 47% light yellow HBr (1.33Kg, 7.7mol) dropwise , after the dropwise addition, the temperature was kept for 3 hours for sampling and analysis; TLC monitoring, when the content of 1,8-dibromooctane reached 3%, was the end of the reaction, cooled to room temperature, and layered, respectively, with 5% NaOH, 10% HCl, The organic layer was washed 3 times with water and saturated sodium bicarbonate solution successively until neutral, and Na 2 SO 4 Dry overnight. The solvent was removed with a rotary evaporator to obtain 1.07kg of 8-bromo-1-octanol, the yield of the product was 73.1%, and the content was >95% by GC inspection.

[0042] b. Synthesis of 8-hydroxyoctyl triphenylphosphine salt

[0043] 8-Bromo-1-octanol (1kg, 4.78mol), triphenylphosphine (1.89kg, 7.17mol) and absolute ethanol (2.5L) were added to the reactor and hea...

Embodiment 3

[0049] a. 8-Bromo-1-octanol synthesis

[0050] 1,8-octanediol (0.73kg, 5mol) and toluene (12.5L) were added to the reactor, stirred and heated to 80-90°C, and 47% of light yellow HBr was slowly added dropwise twice at intervals of half an hour. (0.95Kg, 5.5mol), after the dropwise addition was completed, the temperature was kept for 2 hours for sampling and analysis; TLC monitoring, when the 1,8-dibromooctane content reached 3%, was the reaction end point, cooled to room temperature, and layered, using 5 %NaOH, 10% HCl, water, and saturated sodium bicarbonate solution were successively washed 3 times for each organic layer until neutral, and Na 2 SO 4 Dry overnight. The solvent was removed with a rotary evaporator to obtain 0.87kg of 8-bromo-1-octanol, the product yield was 83.5%, and the content was >95% by GC inspection.

[0051] b. Synthesis of 8-hydroxyoctyl triphenylphosphine salt

[0052] 8-bromo-1-octanol (0.8kg, 3.82mol), triphenylphosphine (1.6kg, 6mol) and dehydr...

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Abstract

The invention provides a synthesis method of grapholitha molesta sex pheromone (Z / E)-8-dodecene acetate. The synthesis method comprises the following steps: (1) by taking methylbenzene or benzene as a solvent and 1,8-octanediol and hydrobromic acid as starting raw materials, performing unilateral bromination reaction to obtain 8-bromooctanol; (2) by taking ethanol as a solvent, adding 8-bromooctanol and triphenylphosphine into a reaction kettle, after the reaction, cooling and separating out 8-hydroxyl octyl triphenylphosphine crystals by taking methylbenzene as an eluent; (3) performing Witting reaction on the 8-hydroxyl octyl triphenylphosphine and n-butyraldehyde under the presence of a catalyst 18-crown ether-6 to obtain (Z / E)-8-dodeceneanol, wherein potassium carbonate is adopted as alkali; and (4) by taking pyridine as a solvent, reacting the (Z / E)-8-dodeceneanol with acetic anhydride or acetyl chloride to obtain (Z / E)-8-dodecene acetate. The method mild in conditions, fewer in steps, high in yield, and suitable for industrial production, and raw materials are easily available.

Description

technical field [0001] The invention relates to the field of chemical synthesis of sex pheromone (sex pheromone) of lepidopteran pests, in particular, the invention relates to the synthesis of sex pheromone (Z / E)-8-dodecene acetate method. Background technique [0002] Graphithamolesta belongs to Lepidoptera, Lepidoptera, also known as Oriental Beetle Moth, Pear Small Fruit Boring Moth, and Peach Heartworm. It mainly damages fruit trees such as pears, apples, peaches, hawthorns, and cherries. For many years, chemical pesticides have been the main control methods for the control of pear carnivora, and its resistance has developed rapidly, and chemical pesticides have caused serious environmental pollution. The sex pheromone of pear worm has the advantages of high activity, non-toxicity, strong specificity, convenient use, no harm to natural enemies, etc. It has a good attracting effect on pear worm and is an effective biological control method. The research of pheromone for...

Claims

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Application Information

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IPC IPC(8): C07C67/08C07C67/14C07C69/145C07C29/32C07C33/025C07C29/62C07C31/36C07F9/54
CPCC07B2200/09C07C29/34C07C29/62C07C67/08C07C67/14C07F9/54C07C31/36C07C33/025C07C69/145
Inventor 马瑞燕相会明刘金龙李捷吴东升
Owner SHANXI AGRI UNIV
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