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6-hydroxy-3-hexenylalkoxymethyl ether compound and method for preparing 3, 13-octadecadiene-1-ol from 6-hydroxy-3-hexenylalkoxymethyl ether compound

A technology of hexenyl alkoxymethyl ether and octadecadiene, applied to 6-hydroxy-3-hexenyl alkoxymethyl ether compound and preparing 3,13-octadecadiene- In the field of 1-alcohol, it can solve problems such as difficult prevention and control, and achieve the effect of high yield

Pending Publication Date: 2022-04-22
SHIN ETSU CHEM IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The poplar moth (Paranthrene tabaniformis) is one of the most serious pests of poplar in the northern hemisphere and is known to be difficult to control

Method used

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  • 6-hydroxy-3-hexenylalkoxymethyl ether compound and method for preparing 3, 13-octadecadiene-1-ol from 6-hydroxy-3-hexenylalkoxymethyl ether compound
  • 6-hydroxy-3-hexenylalkoxymethyl ether compound and method for preparing 3, 13-octadecadiene-1-ol from 6-hydroxy-3-hexenylalkoxymethyl ether compound
  • 6-hydroxy-3-hexenylalkoxymethyl ether compound and method for preparing 3, 13-octadecadiene-1-ol from 6-hydroxy-3-hexenylalkoxymethyl ether compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0301] Embodiment 1: prepare 6-hydroxyl-3-hexynyl methoxymethyl ether (10:R 1 =H)

[0302]

[0303] Methylmagnesium chloride (366.84 g, 4.91 mol) and tetrahydrofuran (1530.16 g) were placed in a reactor at room temperature and stirred at 20°C to 25°C for 4 minutes. After the stirring is completed, 3-butynylmethoxymethyl ether (9:R 1 =H) (517.25 g, 4.50 mol, 99.30% purity) was added dropwise to the reactor. After the dropwise addition was complete, the reaction mixture was stirred at 60°C to 70°C for 5 hours. Subsequently, ethylene oxide (257.69 g, 5.85 mol) was added dropwise at 40°C to 60°C. After the dropwise addition was complete, the reaction mixture was stirred at 60°C to 65°C for 3.5 hours. Next, a solution of acetic acid (800.00 g) in water (1600.00 g) was added to the reaction mixture, followed by phase separation. The aqueous phase was removed to obtain an organic phase. The organic phase thus obtained was concentrated under reduced pressure, and the concentr...

Embodiment 2

[0308] Embodiment 2: preparation (3Z)-6-hydroxyl-3-hexenyl methoxymethyl ether (1:R 1 =H)

[0309]

[0310] At room temperature, the 6-hydroxyl-3-hexynyl methoxymethyl ether (10:R) obtained in Example 1 was 1 =H) (635.95 g, 3.91 mol, purity 97.16%) and P-2Ni catalyst (108.60 g) were placed in the reactor. The reactor was purged with hydrogen at 45°C to 55°C for 7.5 hours with stirring. After confirming that the conversion rate was 100%, water (170.94 g) was added to the reaction mixture, followed by phase separation. The aqueous phase was removed to obtain an organic phase. The organic phase thus obtained was concentrated under reduced pressure, and the concentrate was distilled under reduced pressure to obtain (3Z)-6-hydroxy-3-hexenylmethoxymethyl ether (1:R 1 =H) (612.16g, 3.62mol, purity 94.74%, b.p.=107.2°C to 111.0°C / 0.40kPa (3.0mmHg)), yield 92.58%.

[0311] The following is thus prepared (3Z)-6-hydroxy-3-hexenyl methoxymethyl ether (1:R 1 =H) spectral data.

...

Embodiment 3

[0315] Embodiment 3: preparation (3E)-6-hydroxyl-3-hexenyl methoxymethyl ether (1:R 1 =H)

[0316]

[0317]Lithium aluminum hydride (42.50 g, 1.12 mol) and diethylene glycol dimethyl ether (666.24 g) were placed in a reactor at room temperature, and stirred at 50°C to 55°C for 15 minutes. After the stirring was completed, the 6-hydroxy-3-hexynyl methoxymethyl ether (260.85 g, 1.60 mol, purity 97.03%) obtained according to Example 1 was added dropwise at 50°C to 60°C, and at 130°C to 135°C °C and stirred for 20 hours. After cooling to 20°C to 25°C, tetrahydrofuran (2508.78g), water (42.50g), sodium hydroxide (0.16mol) aqueous solution (170.03g) and diatomaceous earth (Celite) (529.51g) were added successively, and stirred for 12 Hour. After the stirring was completed, the reaction mixture was filtered to obtain an organic phase. The organic phase thus obtained was concentrated under reduced pressure, and the concentrate was distilled under reduced pressure to obtain (3E)...

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Abstract

The present invention relates to a 6-hydroxy-3-hexenyl alkoxymethyl ether compound of the following general formula (1): HOCH2CH2CH = CHCH2CH2OCH2OCH2R1 (1), R1 represents a hydrogen atom, a normal alkyl group having 1 to 9 carbon atoms, or a phenyl group; the invention also relates to a method for preparing a 3, 13-octadecadien-1-ol compound of the following formula (6) from a 6-hydroxy-3-hexenyl alkoxymethyl ether compound (1): CH3 (CH2) 3CH = CH (CH2) 8CH = CHCH2CH2OH (6).

Description

technical field [0001] The present invention relates to 6-hydroxy-3-hexenyl alkoxymethyl ether compounds and processes for preparing 3,13-octadecadien-1-ol compounds therefrom. Background technique [0002] Carmenta chrysophanes is recognized as a pest of persimmons in Australia. It has been reported that the proper timing of application of conventional insecticides effective against the pest is unclear, and the insecticides themselves are not very effective against the pest (Non-Patent Document 1 listed below). The poplar wing moth (Paranthrene tabaniformis) is one of the most serious pests of poplar in the northern hemisphere and is known to be difficult to control. One of the sex pheromones of the poplar moth is a 3,13-octadecadien-1-ol compound (Non-Patent Document 2 listed below). Therefore, biological control methods have attracted people's attention, and the utilization of sex pheromone substances is expected to become one of them. [0003] The 3,13-octadecadien-1-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/26C07C43/315C07C41/20C07C41/22C07C43/313C07F3/02C07C41/30C07C43/30C07C29/128C07C33/035C07C67/08C07C69/14
CPCC07C41/26C07C43/315C07C41/20C07C41/22C07F3/02C07C41/30C07C29/128C07C67/08C07C43/313C07C43/30C07C33/035C07C69/14C07C41/48C07C29/10C07C33/02C07C69/145C07C29/132C07C41/24C07C43/178
Inventor 三宅裕树金生刚长江祐辅
Owner SHIN ETSU CHEM IND CO LTD
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