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Synthesis method of macro cyclic ketone intermediate 14-methyl bicycle [10, 3, 0] pentadecyl-1-alkene

A synthetic method and intermediate technology, applied in organic chemistry, hydrogenation hydrocarbon production, etc., can solve the problems of low yield and high requirements on reaction conditions, and achieve the effects of high reaction yield, simple operation, and low raw material cost

Inactive Publication Date: 2010-01-13
上海力智生化科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The raw materials used in these reactions are generally more expensive, and there are certain dangers, the requirements for the reaction conditions are relatively high, and the total yield of the reaction is not high.

Method used

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  • Synthesis method of macro cyclic ketone intermediate 14-methyl bicycle [10, 3, 0] pentadecyl-1-alkene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] (1) Preparation of 2-methylallyl cyclododecanone (I)

[0028] In the 500mL three-necked bottle, add 60g (0.33mol) cyclododecanone, 40mL toluene, 53g (0.66mol) 50% sodium hydroxide aqueous solution and 2.1g (6.6mmol) tetrabutylammonium bromide, heat up to 40 ° C, 36g (0.4mol) of methallyl chloride was added dropwise under vigorous stirring, and the reaction temperature did not exceed 80°C. After 1 hour of dropwise addition, the reaction was continued for 4 hours. After cooling down to room temperature and separating from the aqueous layer, the organic layer was washed with 3N aqueous hydrochloric acid until neutral. After removing the solvent, distill under reduced pressure, collect the 90-92°C / 2mmHg fraction, and obtain 17.2 g of recovered cyclododecanone (28.6% recovery rate). Continue to collect fractions at 128-134° C. / 2 mmHg to obtain 46.7 g of compound I with a yield of 84%.

[0029] (2) Preparation of 14-methylbicyclo[10,3,0]pentadeca-1,12-diene (II)

[0030] ...

Embodiment 2

[0034](1) Preparation of 2-methylallyl cyclododecanone (I)

[0035] In the 500mL three-necked flask, add 60g (0.33mol) cyclododecanone, 40mL toluene, 53g (0.66mol) 50% sodium hydroxide aqueous solution and 2.3g (6.6mmol) triethylbenzyl ammonium chloride (TEBA), The temperature was raised to 60°C, and 36g (0.4mol) of methallyl chloride was added dropwise under vigorous stirring, and the reaction temperature did not exceed 80°C. After 0.6 hours of dropwise addition, the reaction was continued for 8 hours. After cooling down to room temperature and separating from the aqueous layer, the organic layer was washed with 3N aqueous hydrochloric acid until neutral. After removing the solvent, distill under reduced pressure to recover 18 g of cyclododecanone (30% recovery rate). Continue the distillation under reduced pressure to obtain 47g of compound I with a yield of 85%.

[0036] (2) Preparation of 14-methylbicyclo[10,3,0]pentadeca-1,12-diene (II)

[0037] Fill the reaction tube...

Embodiment 3

[0041] (1) Preparation of 2-methylallyl cyclododecanone (I)

[0042] In a 500mL three-necked flask, add 60g (0.33mol) cyclododecanone, 40mL acetonitrile, 25g (0.6mol) powdered sodium hydroxide and 2g (5mmol) PEG400, add dropwise 36g (0.4mol) methylene Propyl chloride, the reaction temperature does not exceed 60°C. After 0.5 hours of dropwise addition, the reaction was continued for 6 hours. Cool down to room temperature, remove inorganic matter by filtration, and wash the organic layer with 3N aqueous hydrochloric acid solution (30 mL×2) and water (30 mL×2). After removing the solvent, distill under reduced pressure to recover 17g of cyclododecanone (28.3% recovery rate). The vacuum distillation was continued to obtain 48g of compound I with a yield of 86%.

[0043] (2) Preparation of 14-methylbicyclo[10,3,0]pentadeca-1,12-diene (II)

[0044] Fill the reaction tube with 60g of silicon oxide, raise the temperature to 280°C, and at the same time reduce the pressure to mainta...

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Abstract

The invention relates to a synthesis method of macro cyclic ketone intermediate 14-methyl bicycle [10, 3, 0] pentadecyl-1-alkene. The method includes that cyclododecanone by product in petroleum industry is taken as raw material, methacrylic side chain is introduced to alpha site of carbonyl thereof, and dehydration cyclization by alumina and hydrogenation are carried out. The method of the invention is low in raw material cost, steady in reaction and safe and reliable and is applicable to industrialized production.

Description

technical field [0001] The invention relates to a method for synthesizing a macrocyclic ketone intermediate 14-methylbicyclo[10,3,0]pentade-1-ene, which is a key intermediate for synthesizing macrocyclic (n≥15) ketone musk . The synthesis method provided by the invention has low raw material cost, stable reaction, safety and reliability, and is suitable for industrialized production. Background technique [0002] Musk is a rare animal fragrance with strong diffusivity and eliciting power. It has a special soft and elegant fragrance, good fragrance-enhancing effect and excellent fragrance-fixing ability. Musk is not only used as a spice, but more importantly, it has medicinal value. According to the records of the Pharmacopoeia of ancient medical classics in my country: musk has the functions of aromatic resuscitation, soothing the mind, widening the chest, analgesic and calming the nerves, dredging the meridians, promoting blood circulation and removing blood stasis, anti-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C13/32C07C5/05
Inventor 刘锡玲张叶明
Owner 上海力智生化科技有限公司
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