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Synthesis method of trans-4-oxo-2-hexenal

A synthesis method and hexenal technology, applied in the field of chemical production, can solve problems such as the bottleneck of the synthesis method, and achieve the effects of less equipment investment, uniform temperature and controllable reaction conditions, and high safety.

Pending Publication Date: 2020-10-09
SUZHOU HUADAO BIOLOGICAL PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

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Benefits of technology

This patented technology allows for easy access through different routes from other chemical compounds that can be used instead or combined together without changing their properties significantly. It also provides technical benefits such as simplified operation, safe reactions at every step, less expensive starting material compared to previous methods, resulting in increased yields per unit volume over time (up to almost 40-50%).

Problems solved by technology

The technical problem addressed in this patents relating to producing a new type of compound called beta hemiasteroid from natural sources like grasshopper mothers is finding a more efficient way to produce these molecules without generating dangerous waste products due to their complex structure.

Method used

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  • Synthesis method of trans-4-oxo-2-hexenal
  • Synthesis method of trans-4-oxo-2-hexenal
  • Synthesis method of trans-4-oxo-2-hexenal

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preparation example Construction

[0030] Specifically, its synthetic method includes:

[0031] 1. Synthesis Step A: Synthesis of 2-oxobutyltriphenylphosphonium bromide salt

[0032] Make bromobutanone (compound 1) and triphenylphosphine with a molar ratio of 1:1.2~1.5 in an organic solvent (dichloromethane, tetrahydrofuran, methyl tert-butyl ether, benzene, methyl tetrahydrofuran, toluene, acetonitrile or At least one of diisopropyl ether) is heated to reflux reaction, cooled and suction filtered, and dried to obtain 2-oxobutyltriphenylphosphonium bromide salt (compound 2);

[0033] 2. Synthesis Step B: Synthesis of (Ethylcarbonylmethylene) Triphenylphosphine

[0034] The 2-oxobutyl triphenylphosphonium bromide salt (compound 2) is dissolved in an organic solvent (dichloromethane, tetrahydrofuran, methyl tert-butyl ether, benzene, methyl tetrahydrofuran, toluene, acetonitrile or dichloromethane At least one in isopropyl ether), according to the molar ratio of 2-oxobutyltriphenylphosphonium bromide salt and a...

Embodiment 1

[0041] Synthesis of 2-oxobutyltriphenylphosphonium bromide salt (compound 2):

[0042] Dissolve triphenylphosphine (31.5g, 0.12mol) in 150mL tetrahydrofuran, and add bromobutanone (15.1g, 0.1mol) / 50mL tetrahydrofuran solution dropwise under ice-water cooling; after the dropwise addition, stir for 1 hour and heat to reflux Cool to 0°C for 2 hours to crystallize, filter with suction, wash the filter cake with petroleum ether, and dry with an infrared lamp to obtain 39.3 g of 2-oxobutyltriphenylphosphonium bromide salt with a yield of 95%.

Embodiment 2

[0044] Synthesis of (ethylcarbonylmethylene)triphenylphosphine (compound 3):

[0045] Suspend 2-oxobutyltriphenylphosphonium bromide salt (82.6g, 0.2mol) in 500mL ethyl acetate, under vigorous stirring, add potassium tert-butoxide (24.6g, 0.22mol) in batches; Stir for 30 minutes, add ice water and stir rapidly for 5 minutes, statically separate layers, dry the organic phase with anhydrous sodium sulfate, and concentrate to obtain 61 g of (ethylcarbonylmethylene)triphenylphosphine with a yield of 92%.

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Abstract

The invention discloses a synthesis method of trans-4-oxo-2-hexenal. The synthesis method comprises the following steps: bromobutanone and triphenylphosphine are used as initial raw materials; in organic solvents, the compound is prepared by the following synthetic route. By adopting a brand-new synthesis route, the whole synthesis process is simple and convenient to operate, the reaction conditions of each reaction stage are mild and controllable, the safety is high, the equipment investment is low, the yield of each intermediate product is 90% or above, and the yield of the final product trans-4-oxo-2-hexenal is high and is improved by 30% or above compared with the prior art; according to the method, the raw materials which are low in cost and easy to obtain are adopted, and the methodis suitable for industrial production and has important significance in realizing the release production of the sex pheromones of the apolygus lucorum.

Description

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Claims

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Application Information

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Owner SUZHOU HUADAO BIOLOGICAL PHARMA
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