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Aromatic rose ether perfume synthesis method

A technology of aromatic rose ether and synthesis method, which is applied in directions such as organic chemistry, can solve problems such as unfavorable industrial production, equipment corrosion, low reaction yield and the like, and achieves the effect of improving selectivity

Inactive Publication Date: 2019-09-20
国际香料香精(浙江)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these strong acid catalysts are unfavorable in industrial production because they cause corrosion of equipment.
In addition, both the raw material isopentenol and the product are sensitive to strong acid, so the reaction yield is often low
What's more unfavorable is that the strong acidic catalyst will lead to the simultaneous generation of more hydrated pyran by-products (see formula 2), which will bring difficulties for subsequent separation and purification, and further affect the yield of the entire process

Method used

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  • Aromatic rose ether perfume synthesis method
  • Aromatic rose ether perfume synthesis method
  • Aromatic rose ether perfume synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] 387 g (3.65 mol) of benzaldehyde, 400 ml of toluene and 0.73 g of PPTS were added to a one-liter jacketed reactor equipped with mechanical stirring, a Dean-Stark trap and a dropping funnel. (3.0mmol) was heated to reflux for one hour, and 300 grams (3.49mol) of isopentenol was added dropwise over 10 hours. After the dropwise addition, the reaction was continued until the water separator stopped collecting the water generated by the reaction, and cooled to room temperature. Add 200 ml of 5% acetic acid aqueous solution and 200 ml of water to wash successively. After recovering the solvent under reduced pressure, the crude product was purified by rectification to obtain 480 g of dihydropyran product (83-84° C. / 1 mmHg, molar yield 79%).

Embodiment 2

[0028] Into a one liter jacketed reactor equipped with mechanical stirring, Dean-Stark trap and dropping funnel were charged 500 g (4.72 mol) of benzaldehyde, 500 ml of xylene and 0.85 g of PPTS (3.4 mmol). One hour after heating to reflux, 300 grams (3.49 mol) of prenol was added dropwise over 12 hours. After the dropwise addition, the reflux was continued until the water separator stopped collecting the water generated by the reaction, and cooled to room temperature. Add 200 ml of 5% acetic acid aqueous solution and 200 ml of water to wash successively. After recovering the solvent under reduced pressure, the crude product was purified by rectification to obtain 460 g of dihydropyran product (83-84° C. / 1 mmHg, molar yield 75%).

Embodiment 3

[0030] Into a one liter jacketed reactor equipped with mechanical stirring, Dean-Stark trap and dropping funnel were added 387 g (3.65 mol) of benzaldehyde, 180 ml of toluene and 0.35 g of ferric sulfate (0.87 mmol). One hour after heating to reflux, 300 g (3.49 mol) of isopentenol was added dropwise over 8 hours. After the dropwise addition, reflux was continued for one hour, and then heating was stopped and cooled to room temperature. Add 200 ml of 5% acetic acid aqueous solution and 200 ml of water to wash successively. The solvent was recovered under reduced pressure, and the crude product was rectified under reduced pressure to obtain 540 grams of dihydropyran product (83-84°C / 1mmHg, molar yield 89%.)

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Abstract

The invention discloses an aromatic rose ether perfume synthesis method, which comprises: carrying out a complete reaction at a reflux temperature in an inert aprotic solvent by using benzaldehyde and prenyl alcohol as raw materials and using a non-protonic acid or Lewis acid as a catalyst, and carrying out post-treatment on the obtained reaction mixed solution to obtain 4-methyl-2-phenyl-pyran. According to the present invention, the mild catalyst is used, the use equivalent of the catalyst is less than one equivalent of benzaldehyde or prenyl alcohol, the water generated by the reaction is removed by using the azeotropic solvent with water, the selectivity of the reaction is increased, the molar yield of the reaction can be up to about 90%, and the method has characteristics of economy, environmental protection, simpleness and high yield, and is suitable for large-scale industrial production.

Description

technical field [0001] This application relates to a synthetic method of chemical fragrance rose ether fragrance. Background technique [0002] Aromatic rose ether is a mixture of double bond isomers of 4-methyl-2-phenyl-dihydropyran (structural formulas such as I, II and III), with a very strong and transparent rose character, accompanied by Green notes, bay leaves and metallic notes. It is especially suitable for air fresheners with rose and fragrant leaves as the main fragrance type. In addition, aromatic rose ether can also synthesize other important fragrances through chemical transformation, such as dauritol (see US Patent 5219836 and Tetrahedron Letters, 1970,51,4507-4508) and 3-methyl-5-phenylpentanol ( See Swiss patent CH655932 and US patent US 6600079). [0003] Aromatic rose oxide is a mixture of double bond isomers (I, II and III) of 4-methyl-2-phenyl-dihydropyran, the structure of which is shown below: [0004] [0005] Industrially, aromatic rose ether i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/18
CPCC07D309/18
Inventor 徐尚杰方茂海
Owner 国际香料香精(浙江)有限公司
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