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Synthesis method of 8-tert-butyl-2-chloromethyl-1, 4-dioxaspiro [4, 5] decane

A technology of dioxaspiro and synthesis method, which is applied in the field of synthesis of pesticide intermediates, can solve the problems of unsatisfactory reaction yield, many impurities in side reactions, and increased product cost, so as to improve atom utilization rate and reduce side reaction impurities. The effect of less, short reaction time

Inactive Publication Date: 2020-11-10
ZHEJIANG RES INST OF CHEM IND CO LTD +1
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Problems solved by technology

[0007] (1) Patents DE3719326A1 and DE19529090A1 have all reported the method for compound shown in above-mentioned reaction route synthetic formula III, and reaction reagent and condition are p-toluenesulfonyl chloride, pyridine and dichloroethane, but the raw material cost of this synthetic method is higher, increases product cost
[0008] (2) The Chinese invention patent application document whose publication number is CN105817228A has also reported the method for the compound shown in the above-mentioned reaction route synthesis formula III, and the p-tert-butylcyclohexanone shown in the formula I and the 3-chloroglycerol shown in the formula II In the water-carrying agent cyclohexane, fly ash is used as a catalyst to synthesize the compound of formula III, the reaction conversion rate is about 90%, and the reaction yield purity of this synthesis method is not ideal enough
[0009] Therefore, because there are many deficiencies in the above-mentioned traditional synthetic route, such as high raw material price, long reaction time, high energy consumption, many impurities generated by side reactions, etc., therefore, it is necessary to 8-tert-butyl-2-chloromethyl-1, Further improvement on the synthesis method of 4-dioxaspiro[4,5]decane

Method used

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  • Synthesis method of 8-tert-butyl-2-chloromethyl-1, 4-dioxaspiro [4, 5] decane
  • Synthesis method of 8-tert-butyl-2-chloromethyl-1, 4-dioxaspiro [4, 5] decane
  • Synthesis method of 8-tert-butyl-2-chloromethyl-1, 4-dioxaspiro [4, 5] decane

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Experimental program
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Effect test

Embodiment 1

[0028] Add 15.4 g (0.1 mol) of p-tert-butylcyclohexanone (I) and 10.2 g (0.11 mol) of epichlorohydrin (IV) into a three-necked flask with a condensing device, add 60 g of toluene, replace with nitrogen, and stir magnetically Quickly add 0.77 g of tin tetrachloride dropwise, exotherm, heat in an oil bath at 100 ° C for 4 hours, the gas phase detection reaction is complete, cool to room temperature, add 50 ml of water to the reaction system, wash with water three times, let stand to separate liquid, toluene The layer was dried over anhydrous sodium sulfate for two hours, filtered, and the toluene was evaporated to dryness under reduced pressure to obtain the crude product 25 of 8-tert-butyl-2-chloromethyl-1,4-dioxaspiro[4,5]decane grams, the crude product yield is 97.6%, and the GC purity is 95.7%.

Embodiment 2

[0030] Add 15.4 g (0.1 mol) of p-tert-butylcyclohexanone (I) and 10.2 g (0.11 mol) of epichlorohydrin (IV) into a three-necked flask with a condensing device, add 60 g of toluene, replace with nitrogen, and stir magnetically Quickly add 0.77 g of boron trifluoride diethyl ether dropwise, exothermic reaction, heat in an oil bath at 100°C for 5 hours, the reaction is complete by gas phase detection, cool to room temperature, add 50 ml of water to the reaction system, wash with water three times, let stand to separate the liquid, The toluene layer was dried over anhydrous sodium sulfate for two hours, filtered, and the toluene was evaporated to dryness under reduced pressure to obtain the crude product of 8-tert-butyl-2-chloromethyl-1,4-dioxaspiro[4,5]decane as a brown oily product 24.5 g, crude product yield 95.7%, GC purity 95.9%.

Embodiment 3

[0032] Add 15.4 g (0.1 mol) of p-tert-butylcyclohexanone (I) and 11.0 g (0.12 mol) of epichlorohydrin (IV) into a three-necked flask with a condensing device, add 60 g of toluene, replace with nitrogen, and stir magnetically Quickly add 0.77 g of zinc chloride solid, heat in an oil bath at 110 ° C for 12 hours, gas phase detection of the reaction is complete, cool to room temperature, add 50 ml of water to the reaction system, wash with water three times, let stand to separate the liquid, anhydrous sodium sulfate in the toluene layer Dry for two hours, filter, and evaporate toluene under reduced pressure to obtain 18.5 grams of crude product 8-tert-butyl-2-chloromethyl-1,4-dioxaspiro[4,5]decane as a yellow oily product. 72.2%, GC purity 93.9%

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Abstract

The invention discloses a synthesis method of 8-tert-butyl-2-chloromethyl-1, 4-dioxaspiro [4, 5] decane, and the method comprises the following steps: dissolving p-tert-butyl cyclohexanone and epoxy chloropropane in an aprotic solvent, and performing reacting under the catalytic action of Lewis acid to obtain the 8-tert-butyl-2-chloromethyl-1, 4-dioxaspiro [4, 5] decane. According to the method, epoxy chloropropane with lower price is used for replacing 3-chloro-glycerol in a conventional route, so the production cost of the product is reduced; the method has the advantages of mild reaction conditions, high reaction selectivity and few side reaction impurities, and the product can reach high purity and yield, so the method is suitable for large-scale industrial production and application.

Description

technical field [0001] The invention belongs to the field of synthesis of pesticide intermediates, and in particular relates to a synthesis method of 8-tert-butyl-2-chloromethyl-1,4-dioxaspiro[4,5]decane. Background technique [0002] Spiroxamine (spiroxamine) is a substituted amine fungicide successfully developed by Bayer. ,5] decan-2-yl] methyl (ethyl) (propyl) amine, the English name is 8-tert-butyl-1,4-dioxoaspiro [4,5] decan-2-ylmethyl (ethyl) ( propyl)amine, CAS No. 118134-30-8, molecular formula C 18 h 35 NO 2 , molecular weight 297.476. [0003] Mechanism and characteristics of spirulina: sterol biosynthesis inhibitor, mainly inhibits the synthesis of C-14 demethylase. Mainly used in wheat and barley. Control objects: wheat powdery mildew and various rusts; barley moire and streak disease. Safety to crops: Under the recommended dose, it is safe to crops and has no phytotoxicity. Spirulina is a new type of systemic foliar fungicide, which is especially effect...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/72
CPCC07D317/72
Inventor 韦伟张晓铭姚汉清沈方烈李晶王国超
Owner ZHEJIANG RES INST OF CHEM IND CO LTD
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