Preparation method of 1,2-bi-trimethylsilyloxy cyclohexene

A technology of trimethylsiloxane and trimethylchlorosilane, which is applied in the field of 1, can solve the problems of large amount of trimethylchlorosilane, unsuitable for industrialization, high production cost, etc., and achieves less side reactions and less destructiveness , cost-saving effect

Active Publication Date: 2010-06-16
ZHEJIANG NHU CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because the ethyl ester group of diethyl adipate needs to consume trimethyl chlorosilane, the consumption of trimethyl chlorosilane is 4 times molar weight of diethyl adipate, and the consumption of trimethyl chlorosilane is large, and production higher cost
[0006] JP54117441 uses adipic dichloride as raw material, reacts with magnesium foil and trimethylchlorosilane to obtain 1,2-bis-trimethylsiloxane cyclohexene, the yield is 40%, the yield is low, not suitable for industrialization

Method used

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  • Preparation method of 1,2-bi-trimethylsilyloxy cyclohexene
  • Preparation method of 1,2-bi-trimethylsilyloxy cyclohexene

Examples

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Embodiment 1

[0028] In a 500ml three-necked flask equipped with mechanical stirring and a thermometer, put 186g (1.0mol) of adipic acid dichloride and 150ml of methylene chloride, stir and cool to 0°C, and add the mixture of methanol and methylene chloride dropwise at a constant speed for 1 hour[ Methanol 34.5g (1.078mol), dichloromethane 50ml], continue to react at 0 ℃ for 1 hour after dropping, heat up to 15-30 ℃ and react for 1 hour, after the reaction is completed, dichloromethane is distilled under reduced pressure, and the residue is reduced Pressure rectification, collection 107-108 ℃ (10mmHg) is monomethyl adipate monoacyl chloride, weight 164.0g, content 98.0% (GC) yield 90.0%.

Embodiment 2

[0030] Put 186g (1.0mol) of adipic dichloride and 150ml of carbon tetrachloride into a 500ml three-necked flask equipped with mechanical stirring and a thermometer, stir and cool to 0°C, and add anhydrous ethanol and tetrachloride dropwise at a constant speed for 1 hour. Carbon mixture [absolute ethanol 49.5g (1.075mol), carbon tetrachloride 70ml], after dripping, continue to react at 0°C for 1 hour, raise the temperature to 25-30°C and react for 1 hour, after the reaction is completed, tetrachloride is distilled off under reduced pressure. Carbon chloride, rectification under reduced pressure on the residue, collected at 115-117°C (10mmHg) as monoethyl adipate monoacyl chloride, weight 178.0g, content 98.0% (GC) yield 90.5%.

Embodiment 3

[0032] Put 186g (1.0mol) of adipic acid dichloride and 150ml of trichlorethylene into a 500ml three-necked bottle equipped with mechanical stirring and a thermometer, stir and cool to 0°C, and add anhydrous ethanol and trichlorethylene dropwise at a constant speed for 1 hour. Mixture [absolute ethanol 49.5g (1.075mol), trichlorethylene 70ml], continue to react at 0°C for 1 hour after dripping, raise the temperature to 25-50°C for 1 hour, after the reaction is complete, distill off trichlorethylene under reduced pressure, The residue was rectified under reduced pressure and collected at 115-117°C (10mmHg) as ethyl adipate monoacyl chloride, with a weight of 177.8g, a content of 98.0% (GC) and a yield of 90.4%.

[0033] The solvent in above-mentioned embodiment 1-3 also can replace with trichloromethane, tetrachloroethylene, toluene, ethylbenzene, xylene, isopropylbenzene, trimethylbenzene, normal hexane, sherwood oil, hexanaphthene or methylcyclohexane The alcohol used in the r...

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Abstract

The invention discloses a preparation method of 1,2-bi-trimethylsilyloxy cyclohexene. In the traditional methods, some methods have large consumption of trimethyl chlorosilane and higher production cost; and some methods have lower yield and are not suitable for industrialization. The preparation method of the 1,2-bi-trimethylsilyloxy cyclohexene in the invention comprises the step of reacting adipic acid monoalkyl ester monochloride as a raw material with the trimethyl chlorosilane and metal sodium in a solvent to obtain the 1,2-bi-trimethylsilyloxy cyclohexene. Compared with the prior art adopting adipoyl dichloride as a raw material, the method of the invention has mild reaction, less side reactions and high yield; and compared with the prior art adopting diethyl adipate as a raw material, the method of the invention saves the consumption of 1 mol of the trimethyl chlorosilane, and saves the cost.

Description

technical field [0001] The invention relates to the field of fine chemicals, in particular to a preparation method of 1,2-bis-trimethylsiloxane cyclohexene. Background technique [0002] 1,2-bis-trimethylsiloxane cyclohexene is an organic synthesis reagent, used as a C6 building block, has good chemical activity, and has the advantages of mild reaction and high yield in organic synthesis. Journal of Organic Chemistry 2005, 70(5), 1901-1903 used 1,2-bis-trimethylsiloxanecyclohexene for the synthesis of d-biotin. [0003] The structural formula of 1,2-bis-trimethylsiloxane cyclohexene is as follows: [0004] [0005] Synthesis (1971, 236-253) used diethyl adipate as a raw material, and obtained 1,2-bis-trimethylsiloxane cyclohexene by cyclization in toluene with metal sodium and trimethylchlorosilane. The rate is 89%. Because the ethyl ester group of diethyl adipate needs to consume trimethylchlorosilane, the consumption of trimethylchlorosilane is 4 times molar weight o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/18
Inventor 车来滨钱洪胜张甲春王银炳王昌泽
Owner ZHEJIANG NHU CO LTD
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