Preparation method of alpha-damascenone perfume

A damascenone fragrance and technology of damascenone, which is applied in the field of fragrance fine chemicals, can solve the problems of low α-damascenone yield, high cost, short route, etc., and achieve high reaction yield and easy operation , the effect of short route

Inactive Publication Date: 2013-04-24
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Because the yield of α-damascenone synthesized by this process is low and the cost is high, it is not suitable for industrial production. Therefore, on the basis of referring to other documents, we have improved this process ro...

Method used

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  • Preparation method of alpha-damascenone perfume
  • Preparation method of alpha-damascenone perfume
  • Preparation method of alpha-damascenone perfume

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Preparation of 6,10-Dimethylundecane-1,9-dien-4-yn-6-ol

[0017]

[0018] In a suitable reaction bottle, control the temperature at 10-20 °C, add methanol (746 ml) into the suspension of KOH (162 g) in toluene (720 ml), control the temperature at 10-20 °C and stir for 15 minutes. Control the temperature at 10-20 °C, mix CuCl (16 g) and K 2 CO 3 (22 g) was added into the reaction flask, and the temperature was controlled at 10-20°C and stirred for 15 minutes. Control the temperature at 10-20 °C, add dehydrolinalool (304 g) into the reaction flask, after the addition is complete, stir for 15 minutes, then, control the temperature at 10-20 °C, add 3-bromopropene (258 g) Slowly add it dropwise into the reaction flask, and after the addition is complete, control the temperature at 10-20°C for the reaction. Gas chromatography (GC) is used to track the reaction. After the reaction of the raw materials is completed, an appropriate amount of dilute hydrochloric acid is add...

Embodiment 2

[0021] Preparation of 6,10-dimethylundecane-2,5,9-trien-4-one or pseudodamascenone

[0022]

[0023] Add molybdenum acetylacetonate (51 g), dimethyl sulfoxide (43 g), p-methoxybenzoic acid (47 g) and toluene (1198 ml) respectively into a suitable reaction vessel, stir and heat to 100 °C, then add 6,10-Dimethylundecane-1,9-dien-4-yn-6-ol (150 g) was reacted at a temperature of 100 °C. Gas chromatography (GC) monitors until the reaction of the raw materials is complete, the mother liquor is cooled to room temperature, filtered, washed with water, the organic phase is separated, dried over anhydrous sodium sulfate, and precipitated to obtain a crude product with a yield of 92%.

[0024] ESI MS m / z :193 [M+H] + ; 1 H NMR (400 MHz, CDCl 3 ): δ = 6.84-6.74 (m, 1H), 6.15-6.10 (m, 2H), 5.13-5.05 (m, 1H), 2.72-1.84 (m, 10H), 1.65-1.58 (m, 6H).

Embodiment 3

[0026] Preparation of 6,10-dimethylundecane-2,5,9-trien-4-one or pseudodamascenone

[0027]

[0028] Add molybdenum acetylacetonate (25 g), dimethyl sulfoxide (30 g), p-methoxybenzoic acid (12 g) and toluene (868 ml) respectively into a suitable reaction vessel, stir and heat to 100 °C, then add 6,10-Dimethylundecane-1,9-dien-4-yn-6-ol (150 g) was reacted at a temperature of 90 °C. Gas chromatography (GC) monitors that the reaction of the raw materials is complete, the mother liquor is cooled to room temperature, filtered, washed with water, the organic phase is separated, dried over anhydrous sodium sulfate, and the crude product is obtained by precipitation with a yield of 88%.

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Abstract

The invention discloses a preparation method of an alpha-damascenone perfume. A technical scheme adopted by the invention is characterized in that the method comprises the following steps: 1, reacting an initial raw material dehydrolinalool with 3-bromopropylene in a mixed solvent comprising toluene and methanol to obtain 6,10-dimethylundecyl-1,9-diene-4-alkynyl-6-ol; 2, converting 6,10-dimethylundecyl-1,9-diene-4-alkynyl-6-ol obtained in step1 in a solvent comprising toluene and dimethyl sulfoxide at 90-100DEG C under the action of a catalyst to obtain fake damascenone; and 3, converting damascenone in a solvent toluene at 50-60DEG C under the action of a catalyst phosphoric acid supported on active carbon to obtain the alpha-damascenone perfume. The method has the advantages of cheap and easily available raw material, mild reaction conditions, high reaction yield of each step, recycle of the solvents comprising toluene and methanol, and low cost, and is a method suitable for the industrialized production of the alpha-damascenone perfume.

Description

technical field [0001] The invention belongs to the technical field of fragrance fine chemicals, and in particular relates to a method for preparing α-damascenone fragrance by using dehydrolinalool and 3-bromopropene as raw materials. Background technique [0002] α-Damascene (damascene), also known as methyl-turkone, also known as α-dihydrodamascene, is named 1-(2,6,6-trimethyl-2-cyclohexene-1- Base)-2-buten-1-one is a colorless to light yellow liquid, soluble in 95% ethanol in any ratio. It is a trace component isolated from Bulgarian rose oil in 1970. It has a typical rose aroma and a strong fruity and floral aroma. It can be used to prepare various floral and modern essences. It can be used as a spice in various foods and beverages. [0003] There have been many reports on the synthesis of α-damascenone, but there is still a lack of simple and convenient synthetic routes. In 1975, Karl H. Schulte-Elte reported that dehydrolinalool was used as a raw material to synthesi...

Claims

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Application Information

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IPC IPC(8): C07C49/543C07C45/67
Inventor 李伟吕晓孟姜玉钦张玮玮任保齐毛龙飞朱琳侯茜茜郑文涛徐桂清
Owner HENAN NORMAL UNIV
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