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Preparation method of aliphatic cyclo benzylether

A technology of cyclobenzyl ether and aliphatic ring, which is applied in the field of synthesis of aliphatic cyclobenzyl ether, can solve problems such as post-processing troubles and yield improvement, and achieve the effects of shortened reaction time, convenient post-processing, and wide process conditions

Active Publication Date: 2010-05-19
DALIAN NETCHEM CHIRAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the presence of aluminum oxide, a step of filtration is added to the post-reaction treatment, which is cumbersome and the yield still needs to be improved.

Method used

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  • Preparation method of aliphatic cyclo benzylether
  • Preparation method of aliphatic cyclo benzylether

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Add 450g (1.84mol) N-Boc protected cyclohexylamine alcohol and 429.5g (2.21mol, 1.2eq) benzyl bromide in the 5L four-necked round bottom flask that mechanical stirring, thermometer and spherical condenser are housed, 148.7g (0.368 mol, 0.2eq) trioctylmethylammonium chloride, and 1000ml of dichloromethane were stirred evenly; under stirring, 3.2kg of 50% sodium hydroxide solution was added in portions to the reactor, and the temperature of the mixture was controlled not to be higher than 40°C. After the 50% sodium hydroxide solution was added dropwise, the temperature was raised to 40°C and refluxed for 3-4 hours; after the reaction was completed, the temperature was lowered and the stirring was stopped. The layers were separated, retaining the dichloromethane layer. The dichloromethane layer was washed once with 300ml of water. After all the dichloromethane layers were distilled off under reduced pressure to remove most of the dichloromethane (minimum volume), n-hexane...

Embodiment 2

[0025] Add 200g of potassium hydroxide and 200g of water into a 2L four-necked round-bottomed flask equipped with mechanical stirring, a thermometer and a spherical condenser, stir to dissolve, cool to 40°C, then add 52.6g (0.354mol) azidocyclohexanol and 24.1 g (0.07mol, 0.2eq) tetrabutylammonium bisulfate, 500ml toluene and stir well. Under stirring, 49.2 g of benzyl chloride was added dropwise to the reaction mixture, and the temperature of the reaction mixture was controlled at 40±2°C. After the dropwise addition of benzyl chloride was completed, the temperature was raised to 60°C, heated and stirred for 4 hours, cooled down, the stirring was stopped, and layers were separated. The collected toluene solution was washed with 300 ml of semi-saturated saline, the chromatographic content of azidobenzyl cyclohexyl ether was 70%, and the chromatographic yield was 90%.

Embodiment 3

[0027] Add 120g of sodium hydroxide and 120g of water into a 1L four-necked round-bottomed flask equipped with mechanical stirring, a thermometer and a spherical condenser, stir to dissolve, cool down to 40°C, and then add 26.7g (0.21mol) of 2-azidocyclopentane Alcohol and 9.7g (0.042mol, 0.2eq) of trimethylbenzyl ammonium bromide, 35.2g (0.25mol, 1.2eq) of p-methylbenzyl chloride and 500ml of chlorobenzene were stirred, and the temperature of the reaction mixture was controlled at 70±2°C. After the reaction, the temperature was lowered, the stirring was stopped, and the layers were separated. The collected toluene solution was washed with 150 ml of semi-saturated saline, the chromatographic content of azidobenzyl cyclopentyl ether was 68%, and the chromatographic yield was 89%.

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Abstract

This invention involves a preparation method of cyclo-fat benzyl ether. It take cyclo-fat alcohol as raw material, non-water-soluble organic as solvent, at 50% solids alkaline aqueous solution environment, by adding benzyl reagent, stirring and refluxing to obtain cyclo-fat benzyl ether. This invention obtain the product by using phase transfer catalyst to synthesize benzyl, adding small amount ofphase-transfer catalyst in the two-phase reaction system, without joining alumina, and taking toluene and dichloromethane etc. common solvent as solvents, mixing in 50% alkaline environment. Throughthe optimization of processes, the reaction time is shortened considerably; Chromatography absorption rate can achieve 85% to 100%, suit for industrial production.

Description

Technical field: [0001] The present invention relates to the synthetic method of compound, especially the synthetic method of alicyclic benzyl ether. Background technique: [0002] The synthesis of aliphatic cyclobenzyl ether generally adopts the A.W.Williamson method. The alicyclic alcohol forms sodium alkoxide in the presence of a strong base such as sodium hydride, calcium hydride, potassium tert-butoxide or sodium tert-butoxide, and then reacts with benzyl halide to form Ether is formed. However, elimination reactions often occur to produce side reactions of alkenes. Moreover, it is necessary to control the anhydrous and oxygen-free reaction system, adding expensive anhydrous solvents or polar aprotic solvents, although the reaction can be carried out, the reaction conditions are harsh, the operation is inconvenient, the post-treatment is complicated, and there are many side reactions at the same time, the yield is low, and the cost is low. high. [0003] Nouguier et ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C41/09C07C43/184
Inventor 吴星娥管月胡秀坤孙宇扬张学龙王程石作武
Owner DALIAN NETCHEM CHIRAL TECH
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