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Method for synthesizing ethyldivaricatinate and application of ethyldivaricatinate

A technology of ethyl arachidonic acid and a synthesis method is applied in the directions of carboxylate preparation, chemical instruments and methods, applications, etc., and can solve the problems of difficult industrialized mass production, low product yield, expensive bromination reagents, etc. Less oral irritation, avoiding high temperature conditions, and good smoke coordination

Active Publication Date: 2013-08-07
CHINA TOBACCO JIANGSU INDAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Others, such as the report of the former West Germany in the published patent 2,359,233 (1974), use reagents such as N-bromocaprolactone amine to aromatize the β-diketone cyclohexane; but the required reaction time is long, and the bromination reagent is expensive , the yield of the product is not high, it is limited to the sample preparation in the laboratory, and it is difficult to carry out industrial batch production
But, do not see at present the various documents and patent reports about the chemical synthesis of elenic acid ethyl ester

Method used

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  • Method for synthesizing ethyldivaricatinate and application of ethyldivaricatinate

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Comparison scheme
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Embodiment 1

[0040] Organic intermediate (3): the synthesis of 2,4-dioxo-6-propyl-cyclohexane ethyl carboxylate comprises the following steps:

[0041] In a 50ml one-necked flask, weigh 0.71g (10.5mmol) of sodium ethoxide, add 15ml of absolute ethanol solution, and stir until the sodium ethoxide is completely dissolved. Add 1.6g (10mmol) of diethyl malonate (2) and 1.12g (10mmol) of 3-hepten-2-one (1) in sequence, install a condensing reflux and drying device, and heat up to 40°C , reacted for 5 hours. As the reaction progressed, the color of the solution turned yellow, accompanied by the precipitation of a large amount of light yellow powdery solid.

[0042] After the reaction, acidify with hydrochloric acid, extract with dichloromethane, and remove the dichloromethane by rotary evaporation to obtain 1.88 g of ethyl 2,4-dioxo-6-propyl-cyclohexanecarboxylate in a yellow oily liquid, with a yield of 83 %.

[0043] MS(EI): m / z(%)=226(M + , 10), 183(75), 155(20), 143(25), 137(78), 113(40)...

Embodiment 2

[0045] Organic intermediate (4): 3,5-dibromo-2, the synthesis of 4-dihydroxyl-6-propyl benzoic acid ethyl ester, comprises the following steps:

[0046] In a 50ml single-necked flask, add 1.13g (5mmol) of 2,4-dioxo-6-propyl-cyclohexylcarboxylate ethyl ester prepared in Example 1, then add 15ml of acetic acid therein, and stir Make it dissolve evenly; then measure 0.77ml (15mmol) of liquid bromine and add it dropwise to the reaction solution. After the dropwise addition, react at 25°C for 15h.

[0047] After the reaction, the reaction solution was poured into 50ml of water, and a small amount of anhydrous sodium sulfite was added to remove excess liquid bromine to remove the color of the solution. After stirring for a while, a large amount of yellow solid was formed, which was filtered, washed with water, and dried to obtain 1.69 g of yellow solid with a yield of 88%. The obtained yellow solid was separated and purified by silica gel column chromatography, eluted with a mixed ...

Embodiment 3

[0050] Organic intermediate (5): the synthesis of ethyl 2,4-dihydroxy-6-propylbenzoate comprises the following steps:

[0051] 1.14g (3mmol) 3,5-dibromo-2,4-dihydroxyl-6-propyl benzoic acid ethyl ester that embodiment 2 makes is dropped in the single port reaction flask of 50ml, adds 7.5ml 2N NaOH solution, After stirring to make it dissolve, add 0.17g of 10% Cu / Co catalyst, and stir to make the catalyst evenly distributed. Install a three-way valve in the reaction flask, put a hydrogen-filled balloon on the three-way valve, adjust the valve position of the three-way valve, vacuumize the air in the reaction flask, and then adjust the valve to introduce the hydrogen in the balloon into the reaction flask , repeat 1 time. Under the condition of 25°C, the reaction was stirred for 24 hours, and hydrogen was replenished twice by balloon on the way.

[0052] After the reaction, the Cu / Co in the reaction solution was removed with a sand core funnel to obtain a clear brown reaction ...

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Abstract

The invention discloses a method for synthesizing ethyldivaricatinate and application of the ethyldivaricatinate. The method comprises the following steps of: reacting 3-hepten-2-one and diethyl malonate which are taken as raw materials to obtain 3,5-dibromo-2,4-dihydroxy-6-ethyl propylbenzoate; adding liquid bromine to perform bromination aromatization reaction on beta-diketone cyclohexane; performing debromination hydrogenation reaction on a product obtained in the previous step and hydrogen; and finally performing alkylation reaction on an obtained product and dimethyl carbonate (DMC) to obtain a target product. Raw materials and reagents which are used in the method are readily available, the reaction route is short, reaction conditions are mild, and the yield of organic intermediatesand a final product is high; meanwhile, the ethyldivaricatinate also has broader industrial application prospect.

Description

technical field [0001] The invention relates to the field of preparation of flavors and fragrances, in particular to a method for synthesizing the main fragrance component of a moss-flavored fragrance—ethyl arachidinagnatate and its application. Background technique [0002] Moss-flavored spices mainly include tree moss and oakmoss extracts and absolute products, which are all made from a tea-stained lichen plant belonging to the Usneaceae genus Pleurotus genus as raw materials through certain processing techniques . The raw material for the production of tree moss extract and absolute oil is tree moss, and the raw material for oakmoss extract and absolute oil is oak moss. Among them, the raw materials of lichens grown in Yugoslavia, France, Italy and other countries along the Mediterranean coast in central and southern Europe The quality of moss-flavored spices is the best. Due to the limitations of the place of origin of the processed raw materials and the processing tec...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/92C07C67/30A24B15/30
Inventor 朱龙杰庄亚东朱怀远张映万敏熊晓敏刘献军
Owner CHINA TOBACCO JIANGSU INDAL
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