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Preparation method of rose ether

A technology of rose ether and compounds, which is applied in the field of preparation of rose ether, can solve the problems of low reaction yield, increased production cost, and low stereoselectivity, and achieve the effects of high reaction yield, low production cost, and convenient processing

Inactive Publication Date: 2014-03-26
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0025] 1. The use of various highly toxic reagents and metal reagents will inevitably have a negative impact on the environment, and will also increase production costs to a large extent;
[0026] 2. The stereoselectivity of the reaction is not high. So far, various methods have not well controlled the stereoselectivity of the reaction.
[0028] 3. The reaction yield of each route is generally not high

Method used

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  • Preparation method of rose ether

Examples

Experimental program
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Effect test

Embodiment 1

[0070] The preparation method of pure cis-rose ether

[0071] 1) Preparation of corresponding α,β-unsaturated ketones:

[0072] Citronellol (1.0g, 6.4mol) was dissolved in CH 2 Cl 2 (5mL), m-CPBA (1.1g, 6.4mmol) was slowly added in batches at 0°C, and after 30 minutes, diethyl ether (200mL) was added, and the mixture was washed with saturated Na 2 CO 3 solution and saline wash. Anhydrous Na for organic phase 2 SO 4 After drying, the solvent was evaporated under reduced pressure to obtain an epoxy compound.

[0073] The citronellol used in the reaction can be in R configuration, S configuration or a mixture of R configuration and S configuration, and m-CPBA can be replaced by peracetic acid or peroxybenzoic acid.

[0074] Under the protection of argon, the epoxy compound was dissolved in toluene (4 mL), aluminum isopropoxide (1.3 g, 6.4 mmol) was added, and the temperature was raised to reflux for 8 hours. The system was cooled to room temperature and acidified with 2M ...

Embodiment 2

[0091] Preparation method of cis-rose ether and trans-rose ether mixture

[0092] The specific operations of steps 1) and 2) are the same as the steps 1) and 2) of Example 1, the difference lies in step 3), and the specific operations of step 3) are as follows:

[0093] Allene compound (0.77g, 5.0mmol) was dissolved in 10mL of toluene at room temperature, hydrochloric acid (10mmol) was added slowly, and reacted for 20 hours. Add 5 mL of saturated NaHCO 3 The reaction was terminated with the solution, extracted with ether (100 mL), and the organic phase was washed with brine. Anhydrous Na 2 SO 4 After drying, the solvent was evaporated under reduced pressure, and the mixture of cis-rose ether and trans-rose ether (0.38g, 50% yield) was obtained by column chromatography. The ratio of cis-product to trans-product was 1:1.

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Abstract

The invention discloses a preparation method of rose ether. The preparation method of the rose ether comprises the following steps: firstly, with geraniol as a starting raw material, performing epoxidation, epoxy rearrangement and selective oxidation to obtain corresponding alpha, beta-unsatisfied ketone; secondly, combining with phenylsulfonyl hydrazine or a derivative thereof to form a phenylsulfonyl hydrazone intermediate, and obtaining a corresponding olefinic compound through amine catalysis; finally, cyclizing the olefinic compound to obtain the rose ether. In the whole process of the preparation method, no toxic reagent and no expensive metal reagent are used, so that the reaction posttreatment is convenient and the production cost is relatively low; three-dimensional selectivity of the reaction can be controlled by changing reaction conditions, so that synthesis of cis-rose ether or a mixture of cis-rose ether and trans-rose ether is realized; the reaction yield is relatively high.

Description

technical field [0001] The invention relates to a method for preparing rose ether, which belongs to the field of organic synthesis. Background technique [0002] Rose ether, also known as Rose Oxide, is an important spice that exists in Bulgarian rose oil, geranium oil, and various flowers, fruits, wine and even insect secretions. In nature, it exists as (-)-(4R)-cis-body and (-)-(4R)-trans-body, mainly in cis-body, with sharp and penetrating green grass fragrance and rose fragrance. The cis body has a delicate aroma, and its left-handed aroma is sweet, while the trans body has a strong green aroma and some spicy aroma. It is mainly used in rose-type and fragrant-leaf-type flavors, and the dosage is 0.01%-0.2%. A small amount is used in food flavors such as lychee, passion fruit, and black currant. [0003] Industrially, citronellol is mainly used as raw material to prepare rose ether, which can generally be obtained through the following routes: [0004] 1. Photooxidati...

Claims

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Application Information

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IPC IPC(8): C07D309/04
CPCC07D309/04
Inventor 涂永强唐萌
Owner LANZHOU UNIVERSITY
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