Synthesis method of intermediate farnesyl acetone and method for synthesizing phytol, isophytol and geranyl geraniol by using intermediate farnesyl acetone

A technology of farnesyl acetone and synthesis method, which is applied in the direction of carbon-based compound preparation, hydroxyl compound preparation, magnesium organic compound, etc., and can solve the problems of many synthesis steps, reduction of total reaction and hydrogenation reaction steps, etc.

Active Publication Date: 2020-07-10
SHANGHAI MODERN HASEN SHANGQIU PHARMA +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method uses 5-chloro-2-pentanone as a unit to construct geranyl acetone and farnesyl acetone, which reduces the total reaction and hydrogenation reaction steps, but uses acetone and vinyl chloride Grignard when synthesizing methyl heptenone Reaction, and then constructed by Carroll reaction, many synthesis steps

Method used

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  • Synthesis method of intermediate farnesyl acetone and method for synthesizing phytol, isophytol and geranyl geraniol by using intermediate farnesyl acetone
  • Synthesis method of intermediate farnesyl acetone and method for synthesizing phytol, isophytol and geranyl geraniol by using intermediate farnesyl acetone
  • Synthesis method of intermediate farnesyl acetone and method for synthesizing phytol, isophytol and geranyl geraniol by using intermediate farnesyl acetone

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Experimental program
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Effect test

Embodiment 1

[0072] Embodiment 1 synthetic farnesyl acetone

[0073] A kind of synthetic method of intermediate farnesyl acetone, it is raw material with acetone, 5-chloro-2-pentanone, obtains key intermediate farnesyl acetone through three Grignard reactions, specifically comprises the following steps:

[0074] 1) Synthesis of 5-chloro-2-pentanone vinyl ketal:

[0075] Put 600ml of n-heptane, 120.6g (1.00mol) of 5-chloro-2-pentanone, 74.4g (1.20mol) of ethylene glycol and 1.2g (6.3mmol) of p-toluenesulfonic acid into the reaction bottle, install a thermometer and water tank, reflux and water separation reaction for 6 hours. After the reaction was completed, it was lowered to room temperature, and the reaction solution was washed with 100ml of saturated sodium bicarbonate solution, and then washed twice with 100ml of water, and allowed to stand for stratification. The organic layer was dried with anhydrous sodium sulfate, and n-heptane was recovered under reduced pressure. Distillation, ...

Embodiment 2

[0084] Embodiment 2 Phytoketone

[0085] Add 500 ml of ethanol, 100 g (0.38 mol) of farnesyl acetone, 10 g (10%) of Pd / C into the hydrogenation kettle, replace with nitrogen and pass through hydrogen, and stir the reaction at room temperature (25-30°C) at 2 atmospheres until no hydrogen is absorbed (about 24 hours), the reactor was opened after nitrogen replacement, Pd / C was removed by rapid filtration, ethanol was recovered under reduced pressure, and a light yellow transparent liquid was obtained, which was phytoketone (92 g, yield 90%).

Embodiment 3

[0086] Embodiment 3 vinyl chloride Grignard solution

[0087] Add 24.3g (1.0mol) of magnesium powder into a reaction flask equipped with stirring, a thermometer and a dry reflux tube, add 500ml of dry methyl tert-butyl ether, stir, replace the reaction system with dry nitrogen, and then heat up to 50°C, slowly Slowly feed vinyl chloride, and add 1~2 iodine particles at the same time. After the reaction is triggered, the temperature of the system rises, and the color of iodine disappears. and stirring, the reaction solution was cooled to room temperature, and allowed to stand, the supernatant was the vinyl chloride Grignard solution, which was directly used in the next reaction.

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Abstract

The invention relates to a synthesis method of an intermediate farnesyl acetone, and a method for synthesizing vitamin E, vitamin K1, vitamin K2 side chain isophytol, phytol and geranyl geraniol by utilizing farnesyl acetone. Specifically, the method includes: taking acetone and 5-chloro-2-pentanone as the raw materials, carrying out three Grignard reactions to obtain a key intermediate farnesyl acetone, and hydrogenating the farnesyl acetone to obtain phytol ketone; reacting farnesyl acetone with a vinyl chloride Grignard agent to obtain geranyl linalool, and conducting rearrangement under acid catalysis to obtain geranyl geraniol; or reacting the farnesyl acetone directly with a hydroxyl-protected 2-chloroethanol Grignard agent to obtain geranyl geraniol; reacting phytol ketone with a vinyl chloride Grignard agent to obtain isophytol, and rearranging the isophytol under acid catalysis to obtain phytol; or directly reacting the phytol with a hydroxyl-protected 2-chloroethanol Grignardagent to obtain the phytol. The method has the advantages of cheap and easily available initial raw materials, short synthesis process steps, low product cost and the like.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a method for synthesizing an intermediate farnesyl acetone, and using farnesyl acetone to synthesize vitamin E, vitamin K1, and vitamin K2 side chain isophytic alcohol, phytoalcohol, and geranyl The geraniol approach. Background technique [0002] Isophytol is the main raw material for the production of vitamin E and vitamin K1. It is a diterpene lipophilic fatty chain composed of four isoprene units, especially for the production of vitamin E. The demand is large. Phytol, also known as phytol, is a diterpene lipophilic fatty chain composed of four isoprene units. It is a branched chain of chlorophyll, which determines the fat solubility of chlorophyll. It is the main raw material for the synthesis of vitamin K1. Geranylgeraniol is also a diterpene lipophilic fatty chain composed of four isoprene units. It has a wide range of physiological activities, such a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/74C07C45/59C07C47/21C07C45/62C07C47/02C07C29/40C07C29/56C07C33/02C07C29/36C07C33/03
CPCC07D317/16C07F3/02C07C45/74C07C45/59C07C45/62C07C29/40C07C29/56C07C29/36C07C47/21C07C47/02C07C33/02C07C33/03Y02P20/55
Inventor 王英利张培金建闻陈洪吴泉韦威郭旭光秦芳青王海霞刘砺
Owner SHANGHAI MODERN HASEN SHANGQIU PHARMA
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