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Preparation method for octacosanol

A technology of octacosanol and octacosyloxy, which is applied in the field of organic synthesis, can solve the problems of poor atom economy and low efficiency, and achieve the effects of low toxicity, simple process and easy industrialization

Inactive Publication Date: 2009-10-21
XIAMEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Some of these methods are limited by raw materials and some have poor atom economy, so the efficiency is low

Method used

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  • Preparation method for octacosanol

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Experimental program
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Effect test

Embodiment 1

[0032] Step 1: Preparation of 10-bromo-n-decyl alcohol (2)

[0033] Add 1,10-decanediol (1) (11.6g, 67mmol) and toluene (200mL) into a 500mL three-necked flask equipped with a water separator, flow condenser and constant pressure dropping funnel, and use The oil bath was heated to reflux. After the solid was dissolved, 40% HBr (16.3 mL, 80 mmol) was slowly added dropwise from the dropping funnel, and the water generated by the reaction was separated from the water separator. After the conversion of (1) is complete, cool to room temperature and transfer to a separatory funnel, wash with saturated sodium bicarbonate (100mL), (100mL) and saturated sodium chloride (100mL) successively, dry over anhydrous sodium sulfate, and filter The toluene was distilled off under reduced pressure, and the crude product was subjected to flash column chromatography or distillation under reduced pressure to obtain 10-bromo-n-decanol (2) (14.3 g, 90%) as an oily liquid. IR (film, cm -1 )v max : ...

Embodiment 2

[0043] Similar to Example 1, the difference is that the solvent used in step 2 is dichloromethane, and the amount of p-toluenesulfonic acid is 0.2 molar multiples of (2).

Embodiment 3

[0045] Similar to Example 1, the difference is that the solvent used in step 4 is anhydrous ether, and the concentration of 2-(10-bromo-n-decyloxy)-tetrahydropyran (3) in anhydrous ether is 0.2mol / L, the temperature of the coupling reaction is -40°C, the amount of cuprous iodide is 0.45 mole multiple of (3), and the reaction time after adding octadecylsulfonate (6, R=Ts) is 2h.

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Abstract

The invention discloses a preparation method of octacosanol, relates to a preparation method of higher alcohols, in particular relates to a preparation method of octacosanol, and belongs to the field of organic synthesis. Provided is a method for preparing octacosanol with abundant raw material sources, simple process, high yield and purity, and easy large-scale production. Preparation of 10-bromo-n-decyl alcohol (2), preparation of 2-(10-bromo-n-decyloxy)-tetrahydropyran (3), preparation of octadecylsulfonate (6), preparation of protected octadecane Alcohol 2-octadecanoyloxy-tetrahydropyran (7), preparation of octacosanol (8). The raw material is easy to obtain, the process is simple, the chemical yield is high, the product purity is high, the industrialization is easy and the environment is friendly.

Description

technical field [0001] The invention relates to a method for preparing higher alcohols, in particular to a method for preparing octacosanol, and belongs to the field of organic synthesis. Background technique [0002] Octacosanol is a straight-chain alcohol compound with 28 carbon atoms, which mainly exists in animal and plant waxes and plant germs, leaves, stems, fruits and other tissues. Octacosanol has many important functions such as improving physical strength, enhancing endurance, energy, improving reaction sensitivity and stress ability, increasing the body's metabolic rate, improving myocardial function, reducing serum cholesterol and triglyceride levels, and reducing systolic blood pressure. Physiological effects, and also have certain auxiliary treatment and prevention effects on certain diseases. Therefore, in recent years, octacosanol has been widely used as a food additive, etc., and has become a new type of product in the health food industry. [0003] Howeve...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C29/00C07C31/02
Inventor 张洪奎张浩元
Owner XIAMEN UNIV