Low-cost preparation method of ambrogyl ether

A low-cost technology for ambroxide, applied in the preparation of organic compounds, chemical instruments and methods, preparation of hydroxyl compounds, etc., can solve the problems of complex ambroxide reaction steps, high operating labor costs, expensive catalysts and the like , to achieve the effect of ensuring reaction yield and safety, reducing catalyst cost, energy consumption and low cost

Pending Publication Date: 2022-01-14
广州百花香料股份有限公司
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  • Abstract
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Problems solved by technology

[0005] The primary purpose of the present invention is, aiming at the defects and deficiencies of the prior art, solve the technical problems of complex reaction steps of ambrox and high labor cost of operation in the prior art, provide a simplified flow process step, and reduce the reduction of reaction cost. Preparation method of ambrox
[0006] Another object of the present invention is to solve the technical problems of expensive catalyst itself, poor safety and low yield in the prior art, and provide a method for preparing Ambrox in view of the defects and deficiencies of the prior art

Method used

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  • Low-cost preparation method of ambrogyl ether
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preparation example Construction

[0032] Such as figure 1 , 2 Shown, the Ambrox preparation method of the present invention comprises:

[0033] In step 1, sclareolide uses r-based sulfonic acid and a borohydride compound of a monovalent metal as a catalyst to carry out a reduction reaction in a solvent to generate ambroxol;

[0034] The r group can be methyl or tolyl or dodecyl;

[0035] The monovalent metal borohydride compounds include potassium borohydride, sodium borohydride, lithium borohydride and the like.

[0036] Step 2, the reduction reaction of Ambroxol with r-sulfonic acid as a dehydrating agent generates Ambrox;

[0037] The r-based sulfonic acid is used as a catalyst for the first step reaction to strengthen the formation of acid centers, reduce the pH of the reaction system, and reduce the generation of saponification by-products as much as possible; it is also used as a dehydrating agent for the second step reaction; this makes the whole reaction The process is completed coherently and can ...

Embodiment 1

[0046] 5.0 g of sclareolide (0.02 mol), 5.0 g of potassium borohydride (0.09 mol), and 50 g of absolute ethanol were placed in a 250 ml three-necked flask, and refluxed and stirred at 80°C for reaction. After the start of reflux, 4.0 g of methanesulfonic acid (0.04 mol) was dissolved in 10 g of ethanol, and slowly added dropwise to the reaction system. The dropwise addition was complete within 2 hours, and the reaction was continued for 6 hours with reflux and stirring after the drop was completed. The reaction process was monitored by HPLC. After the reaction was complete, the ethanol in the bottle was vacuum-drained, 50 ml of cyclohexane and 2 g of methanesulfonic acid were added, and the reaction was refluxed for 8 hours for dehydration. After the reaction was complete, wash twice with 30 ml of saturated brine, and remove the cyclohexane from the organic layer with a rotary evaporator to obtain 4..2 g of crude Ambrox. Recrystallized with ethanol to obtain 3.0 g of Ambrox prod...

Embodiment 2

[0048] Put 5.2g of sclareolactone, 6g of potassium borohydride, and 42g of ethanol into a 250ml three-neck flask, stir, and heat up to a system temperature of about 78°C, reflux and stir for reaction. After reflux, dissolve 0.5g of methanesulfonic acid in 5g of ethanol, slowly drop Add it to the reaction system, drop it in about 2 hours, and continue to reflux and stir for 8 hours. After the reaction of the raw materials is complete, the ethanol in the bottle is drained under negative pressure, 50ml of cyclohexane and 4g of methanesulfonic acid are added, and the solution is refluxed and dehydrated for 8 hours. After the reaction was complete, wash twice with 30 ml of salt water, remove cyclohexane from the organic layer with a rotary evaporator to obtain 3.5 g of crude Ambrox. Recrystallized with ethanol to obtain 1.8 g of Ambrox product, with a total yield of 34.6%.

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Abstract

The invention provides a low-cost norambrota ether preparation method, which comprises: dissolving sclareolide in a first organic solvent, adding a catalyst, and carrying out a reduction reaction on sclareolide under a heating condition to generate ambradiol, wherein the catalyst is a boron hydride of r-group sulfonic acid and a monovalent metal; and after the first organic solvent is removed, adding a second organic solvent , and using the r-based sulfonic acid in the first-step reaction as a dehydrating agent to continue the reduction reaction. Compared with the prior art, the method has the advantages that the r-based sulfonic acid is used as the catalyst for the first-step reaction and has the effects of enhancing the formation of an acid center, reducing the pH value of a reaction system and reducing the generation of saponification byproducts as much as possible; the r-based sulfonic acid is also used as the dehydrating agent for the second-step reaction; therefore, the whole reaction process is continuously completed and can be carried out in the same reaction container, the reaction operation steps are simplified, the production efficiency is improved, and the reaction cost is reduced.

Description

technical field [0001] The invention relates to the technical field of perfume synthesis, in particular to a method for preparing ambrox with low cost. Background technique [0002] Natural ambergris is a high-grade spice, which comes from the gray-white soft stones in the stomach of sperm whales, and the amount is very small. Ambrox is a synthetic ambergris-flavored spice used as a substitute for natural ambergris. Ambrox's "ambergris effect" can greatly improve the diffusion of flavors. It is used in the flavors of high-end perfumes and cosmetics. It is non-irritating to the human body and is suitable for the skin, hair and fabrics. Fragrance and fixative for creams and shampoos, etc. The raw material of ambergris flavor can also be used in cigarettes, and it is the key aroma-generating component of cigarettes. Ambrox is one of the spices with a particularly prominent effect, which makes an important contribution to the smoke of mixed cigarettes. [0003] In the prior a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/92C07C29/147C07C35/36B01J31/02
CPCC07D307/92C07C29/147B01J31/0225B01J23/04B01J35/0006C07C2602/10B01J2231/643B01J2231/4288C07C35/36
Inventor 吴习荧庄子翀张建斌叶欣怡叶敏怡白济嘉宋玢
Owner 广州百花香料股份有限公司
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