Process for preparing 6-isopropenyl-3-methyl-9-decenyl acetate and intermediates thereof
A technology of decenyl acetate and isopropenyl, applied in the field of sex pheromone substances of citrus pests - California red round scale), can solve problems such as interference with mating methods and difficulties
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[0182] The present invention will be further described with reference to the following examples. It should be understood that the present invention is not limited to or by these Examples.
[0183] Unless otherwise specified, the term "purity" used herein refers to the area percentage in gas chromatography (hereinafter also referred to as "GC"). The term "production ratio" refers to the ratio of the area percentages obtained by GC.
[0184] The term "yield" is calculated from the area percentage obtained by GC.
[0185] Taking into account the purity (% GC) of the starting material and product, the yield was calculated according to the following equation.
[0186] Yield (%)={[(mass weight of reaction product x% GC) / molecular weight of product]÷[(weight mass of raw material in reaction x%GC) / molecular weight of raw material]}×100
[0187] The term "crude yield" refers to the yield of the crude product obtained without purification.
[0188] In the examples, the monitoring of...
Synthetic example 1
[0190] Synthetic Example 1: Preparation of 2-isopropenyl-5-hexenyl chloride (7:X 2 =Cl)
[0191]
[0192] Charge 2-isopropenyl-5-hexenol (19.90 g: 0.118 mol), pyridine (22.46 g: 0.284 mol) and dimethylformamide (DMF) (50 ml) into the reactor under nitrogen atmosphere and Cool to 5 °C. Then, methanesulfonyl chloride (MsCl) (22.77 g: 0.199 mol) was added dropwise to the reactor at 10° C. or less within 1 hour. After the dropwise addition was completed, the mixture was stirred at room temperature (20°C to 25°C) for 1 hour, and then at 100°C to 110°C for 6 hours. The mixture was then cooled to 15°C, and purified water (100 g) and hexane (100 g) were added and stirred for 30 minutes. After stirring was complete, the organic phase was separated. The separated organic phase was worked up, i.e. washed, dried and concentrated, to obtain the crude product 2-isopropenyl-5-hexenyl chloride (7:X 2 =Cl) (17.00 g). The crude product was distilled under reduced pressure to obtain the...
Embodiment 1
[0198] Embodiment 1: Preparation of 5-isopropenyl-2-methyl-8-nonenyl chloride (4:X 1 =Cl)
[0199]
[0200] Magnesium (1.97 g: 0.08 mol) and tetrahydrofuran (THF) were charged into the reactor under a nitrogen atmosphere, heated to 60° C., and stirred for 15 minutes. Then within 25 minutes, the 2-isopropenyl-5-hexenyl chloride prepared in Synthesis Example 1 (7:X 2 =Cl) and tetrahydrofuran (THF) (15.2 g) was added dropwise to the reactor. After completion of the dropwise addition, the mixture was stirred at an internal temperature of 75°C to 80°C for 2 hours to obtain 2-isopropenyl-5-hexenylmagnesium chloride (5). The resulting 2-isopropenyl-5-hexenylmagnesium chloride (5) was cooled to room temperature.
[0201] In another reactor under a nitrogen atmosphere, cuprous iodide (CuI) (0.14 g: 0.0007 mol), lithium nitrate (LiNO 3 )(0.05g:0.0007mol), triethyl phosphite (P(OEt) 3 ) (0.33g:0.002mol), tetrahydrofuran (THF) (15.2g) and 1-bromo-3-chloro-2-methylpropane (6:X 1 =...
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