Synthetic method of triene insect sex attractant
A synthetic method and insect-based technology, which are applied in the field of synthesis of triene-based insect sex attractants, can solve the problems of few literature reports on the chemical synthesis of triene-based sex pheromones, the difficulty of synthesizing the second type of sex pheromone, and the intermediate The product needs to be separated and other problems to achieve the effect of high yield, low cost and easy separation
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Embodiment 1
[0022] Synthesis method of cis,cis,cis-3,6,9-nonadecatriene
[0023] (1) Add 4.5g LiAlH 4 With 80mL of anhydrous ether, under the protection of nitrogen, slowly drop 25g of α-linolenic acid ethyl ester and 80mL of anhydrous ether into the flask in the constant pressure dropping funnel for 60min, and keep stirring. After the dropwise addition, Heat to reflux for 1h, then cool to room temperature, add a small amount of distilled water to hydrolyze the excess LiAlH in an ice-water bath 4 , and then acidified with 5% dilute sulfuric acid until clarified, the mixture was transferred to a separatory funnel, extracted three times with ether and the organic phases were combined, washed with saturated sodium chloride until neutral, dried over anhydrous sodium sulfate for 12 hours, evaporated and distilled under reduced pressure to obtain α-linalenol 25g, the productive rate is 80%.
[0024] (2) In a 250mL standard ground three-neck flask equipped with a constant pressure droppi...
Embodiment 2
[0028] Synthetic method of cis, cis, cis-3,6,9-eicosatriene
[0029] (1) Add 8.5g LiAlH 4 With 160mL of anhydrous ether. Under the protection of nitrogen, slowly drop 65g of ethyl α-linolenic acid and 160mL of anhydrous ether into the flask in the constant pressure dropping funnel for 1-2 h, and keep stirring. After the dropwise addition, heat to reflux for 1- 3h, after the reaction is over, cool to room temperature, add a small amount of distilled water to hydrolyze the excess LiAlH in an ice-water bath 4 , and then acidified with 15% dilute sulfuric acid until clear, the mixture was transferred to a separatory funnel, extracted three times with ether and combined organic phases, washed with saturated sodium chloride until neutral, and dried over anhydrous sodium sulfate for 48h. Evaporate the solvent and distill under reduced pressure to obtain 65 g of α-linolenic alcohol with a yield of 80%.
[0030] (2) In a 250mL standard ground three-neck flask equipped with a c...
Embodiment 3
[0034] Synthetic method of cis, cis, cis-3,6,9-undecatriene
[0035] (1) Add 6.5g LiAlH 4 With 100mL of anhydrous ether. Under the protection of nitrogen, slowly drop 40g of ethyl α-linolenic acid and 90mL of anhydrous ether into the flask in the constant pressure dropping funnel for 1-2h, and keep stirring. After the dropping is completed, heat and reflux for 2-3h , after the reaction is over, cool to room temperature, add a small amount of distilled water to hydrolyze the excess LiAlH in an ice-water bath 4 , and then acidified with 10% dilute sulfuric acid until clarified, the mixture was transferred to a separatory funnel, extracted three times with ether and the combined organic phase was washed with saturated sodium chloride until neutral, and dried over anhydrous sodium sulfate for 30 h. Evaporate the solvent and distill under reduced pressure to obtain 52 g of α-linolenic alcohol with a yield of 78%.
[0036] (2) In a 250mL standard ground three-neck flask equ...
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