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1-haloalkadiene and process for preparing same and process for preparing (9e,11z)-9,11-hexadecadienyl acetate

A technology of carbadienyl acetate and halogenated diene, applied in the field of 1-halogenated diene and its preparation and (9E,11Z)-9,11-hexadecadienyl acetate, Can solve problems such as outbreaks

Active Publication Date: 2019-10-29
SHIN ETSU CHEM IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Pest control of the hickory nut borer with insecticides can lead to outbreaks of secondary pests such as aphids, mites, and leaf miners because the insecticides also kill natural enemies of these secondary pests

Method used

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  • 1-haloalkadiene and process for preparing same and process for preparing (9e,11z)-9,11-hexadecadienyl acetate
  • 1-haloalkadiene and process for preparing same and process for preparing (9e,11z)-9,11-hexadecadienyl acetate
  • 1-haloalkadiene and process for preparing same and process for preparing (9e,11z)-9,11-hexadecadienyl acetate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0223] Preparation of (7E,9Z)-1-chloro-7,9-tetradecadiene (1-1:X=C1)

[0224] 1-Bromopentane (185g, 1.20mol), triphenylphosphine (321g, 1.20mol) and N,N-dimethylformamide (225g) were added to the reactor, and the resulting mixture was heated at 110-115°C Stir for 6 hours to prepare pentyltriphenylphosphonium bromide. The reaction mixture was cooled to 20˜30° C., and tetrahydrofuran (967 g) was added thereto. Then, it was cooled to 0˜10° C., and potassium tert-butoxide (139 g, 1.20 mol) was added thereto. Stir at 10-15°C for 30 minutes, then add (2E)-9-chloro-2-nonenal (2-1: X=C1) (171 g, 0.978 mol) dropwise at -5 to 5°C. After the dropwise addition was complete, the reaction mixture was stirred for 3 hours and then quenched by adding water (593 g) to the reaction mixture. After removing the aqueous layer by liquid-liquid separation, the organic layer was concentrated by evaporating the solvent in vacuo. Then, hexane (713 g) was added to precipitate triphenylphosphine oxi...

Embodiment 2

[0230] Preparation of (8E,10Z)-1-chloro-8,10-pentadecadiene (1-3:X=C1)

[0231] Magnesium (17.8 g, 0.733 g atom) and tetrahydrofuran (198 g) were added to the reactor, and the resulting mixture was stirred at 60-65° C. for 30 minutes. Then, (4E,6Z)-1-chloro-4,6-undecadadiene (4-1:X1=Cl) (124g, 0.667mol) was added dropwise at 60-70°C, and the resulting mixture was heated at 70 Stir at ~75°C for 6 hours to prepare (4E,6Z)-4,6-undecadienylmagnesium chloride. In another reactor was charged cuprous iodide (1.27 g, 0.00667 mol), triethyl phosphite (2.66 g, 0.0160 mol), 1-bromo-4-chlorobutane (131 g, 0.767 mol) and tetrahydrofuran ( 66.1 g), and the resulting mixture was stirred at 0-5°C for 30 minutes. Then, the solution of (4E,6Z)-4,6-undecadienylmagnesium chloride prepared above in tetrahydrofuran was added dropwise at 5-15°C. After completion of the dropwise addition, the reaction mixture was stirred at 5˜10° C. for 2 hours, and then the reaction was stopped by adding ammoni...

Embodiment 3

[0237] Preparation of (9E,11Z)-1-chloro-9,11-hexadecadiene (1-2:X=Cl)

[0238] Magnesium (13.1 g, 0.540 g atom) and tetrahydrofuran (146 g) were added to the reactor, and the resulting mixture was stirred at 60-65° C. for 30 minutes. Then, (4E,6Z)-1-chloro-4,6-undecadadiene (4-1:X 1 =C1) (91.7g, 0.491mol), and then the resulting mixture was stirred at 70-75°C for 6 hours to prepare (4E,6Z)-4,6-undecadienylmagnesium chloride. In another reactor was charged cuprous iodide (0.98 g, 0.0049 mol), triethyl phosphite (1.96 g, 0.0118 mol), 1-bromo-5-chloropentane (105 g, 0.565 mol) and tetrahydrofuran ( 48.7 g), and the resulting mixture was stirred at 0-5°C for 30 minutes. Then, the solution of (4E,6Z)-4,6-undecadienylmagnesium chloride prepared above in tetrahydrofuran was added dropwise at 5-15°C. After the dropwise addition was complete, the resulting reaction mixture was stirred at 5-10° C. for 3 hours, and then stopped by adding ammonium chloride (4.63 g), 20% by weight aqu...

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Abstract

The object of the invention is to prepare (9E,11Z)-9,11-hexadecadienyl acetate with a good yield and high purity. The present invention provides a process for preparing a 1-haloalkadiene of the general formula (1): CH-(CH)-CH=CH-CH-CH-(CH)-X, comprising a step of conducting a Wittig reaction between a haloalkenal of the general formula (2): OHC-CH=CH-(CH)-X, and a triarylphosphonium pentylide of the general formula (3): CH-(CH)-CH-PAr, to obtain the 1-haloalkadiene, and the use of a (7E,9Z)-1-halo-7,9-tetradecadiene obtained by the process for a process of preparing (9E,11Z)-9,11-hexadecadienyl acetate.

Description

technical field [0001] The invention relates to a method for preparing (9E,11Z)-9,11-hexadecadienyl acetate from 1-haloalkadiene. Background technique [0002] The hickory nut borer (Acrobasis nuxvorella) is a serious pest of hickory nuts, which enters pecans by punching holes and feeds in the nuts. Pest control of the hickory nut borer with insecticides can lead to outbreaks of secondary pests such as aphids, mites, and leafminers because the insecticides also kill the natural enemies of these secondary pests. Therefore, people hope that sex pheromones can be used to disrupt mating. [0003] (9E,11Z)-9,11-Hexadecadienal and (9E,11Z)-9,11-Hexadecadienyl acetate were identified as groups of natural sex pheromones of Hickory nut moth points (Non-Patent Documents 1 and 2). [0004] Harris et al. describe a method for the preparation of (9E,11Z)-9,11-hexadecadienyl acetate, in which by the reaction of (E)-1,2-dichloroethene with 1-hexyne (1E)-1-Chloro-1-octen-3-yne derived f...

Claims

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Application Information

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IPC IPC(8): C07C17/263C07C21/04C07C67/08C07C69/145C07F3/02C07C29/36C07C33/02
CPCC07C17/2635C07C21/04C07C67/08C07F3/02C07C29/36C07B2200/09C07C69/145C07C33/02C07C17/2632C07C67/11Y02P20/55C07C21/19C07C29/124C07C67/03C07C69/587
Inventor 渡部友博三宅裕树金生刚
Owner SHIN ETSU CHEM IND CO LTD
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