Preparation method of (cis-9, tans-11)-tetradecadienoic-1-acetic ester
A technology of tetradecadiene and acetate, which is applied in the field of artificial synthesis of insect sex pheromones, can solve the problems of long steps, affecting males of Spodoptera litura, and unfavorable large-scale production, and achieves low cost and good effect , the effect of mild reaction conditions
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
Embodiment 1）
[0035] All reagents used in this example were purchased from Sigma-Aldrich Company with a purity of ≥98%, and were not further processed before use.
[0036] See figure 1 , The synthesis method of (cis 9, trans 11)-tetradecadiene-1-acetate in this embodiment specifically includes the following steps:
[0037] ① Preparation of 9-bromo-1-nonanol:
[0038] Add 18g (113 mmol) of 1,9-nonanediol (purity ≥ 98%), 300 mL of toluene (purity ≥ 98%) and 15.3 mL (135.6 mmol) of 48 wt% aqueous hydrobromic acid into a 500 ml round bottom flask During the process, the temperature was raised to reflux under stirring, and the temperature was 120°C at this time, so that the reaction of generating 9-bromo-1-nonanol occurred, and the stirring and reflux reaction was continued for 28 hours.
[0039] Qualitative analysis by thin-layer chromatography (TLC) showed that some 1,9-nonanediol remained unreacted. The thin-layer plate of TLC was a 60-mesh silica gel plate, and the developer was n-hexane ...
Embodiment 2）
[0067] See figure 2 , Steps ① to ③ of the synthesis method of (cis 9, trans 11)-tetradecadiene-1-acetate in this embodiment are the same as in Example 1, and steps ④ and ⑤ are different from Example 1. The difference is:
[0068] ④Preparation of 9,11-tetradecadien-1-acetate: transfer the 9,11-tetradecadien-1-ol obtained in step ③ into a 100 ml round bottom flask, add 16 mL of Hydropyridine was completely dissolved, and then 13 mL of acetyl anhydride was added to the round-bottomed flask at room temperature to generate 9,11-tetradecadiene-1-acetate; stirred at room temperature for 2 hours to allow the reaction to After completion, the reacted mixture was poured into a 250mL Erlenmeyer flask filled with 150g of crushed ice, and extracted with 4×100mL hexane (the hexane extracts were combined after 4 extractions). The hexane layer was washed with dilute hydrochloric acid, saturated sodium bicarbonate solution, water and saturated brine, and dried over anhydrous sodium sulfate....
Embodiment 3）
[0073] The rest of the synthetic method of this example is the same as that of Example 1, except that: step ④ uses equimolar (that is, the molar number is 12% of the total molar number of the isomer mixture) 4-phenyl-1,2,4- Triazolin-3,5-dione (PTAD) was reacted with 9,11-tetradecadien-1-ol mixture instead of TCNE, and the operation was the same as in Example 1.
[0074] Among them, 4-phenyl-1,2,4-triazoline-3,5-dione cannot react with (cis 9, trans 11)-tetradecadien-1-ol due to steric hindrance,
[0075]
[0076] No D-A adduct in the above reaction formula means that there is no Diels-Alder reaction product.
[0077] And the Diels-Alder reaction of 4-phenyl-1,2,4-triazoline-3,5-dione with (trans 9, trans 11)-tetradecadien-1-ol is:
[0078]
[0079] D-A adduct in the above reaction formula means Diels-Alder reaction product.
PUM
Login to View More Abstract
Description
Claims
Application Information
Login to View More 
PatSnap Eureka turns technology decisions into work you can execute. Powered by our Innovation Knowledge Graph, it runs expert workflows across engineering, life sciences, materials and intellectual property. Get your review-ready output in minutes.
