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Method for preparing methyl dihydrojasmonate

A technology of methyl dihydrojasmonate and dihydrojasmonic acid, which is applied in the field of synthesizing methyl dihydrojasmonate with organic zinc reagents, can solve the problems of complex production process, long synthesis route, and difficult preparation of raw materials , to achieve the effect of cheap and easy-to-obtain raw materials, low cost, and shorten the synthesis cycle

Inactive Publication Date: 2009-09-02
NORTHWEST NORMAL UNIVERSITY
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Problems solved by technology

The raw materials of these methods are not easy to obtain, the manufacturing process is complicated, and the synthetic route is long.

Method used

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  • Method for preparing methyl dihydrojasmonate
  • Method for preparing methyl dihydrojasmonate
  • Method for preparing methyl dihydrojasmonate

Examples

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Embodiment Construction

[0022] The present invention will be further described through specific implementation below.

[0023] Step 1: Preparation of 2-pentylcyclopentenone

[0024] 2-pentylcyclopentenone can be purchased from the market, and can also be prepared by the following processes:

[0025] NaOH (0.83g), H 2 O (75ml) was added into the three-necked flask, heated to 25°C with a water bath, and cyclopentanone (38g) was added dropwise from the dropping funnel, keeping the reaction temperature not exceeding 32°C during the dropwise addition, and then adding n-valeraldehyde (22g ), keep the temperature of the reaction solution not exceeding 32°C. After the addition, react at 28° C. for 1 h, add acetic acid (1.5 g) and stir for 2 min, separate the organic layer, and wash once with saturated brine.

[0026] Add NaHSO 4 The solution was stirred at room temperature for 20 min, and a small amount of n-butanol was added. The organic layer was separated and washed once with saturated saline solutio...

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Abstract

The invention provides a method for synthesizing methyl dihydrojasmonate. 2-pentyl cyclopentenone is adopted as a raw material; the raw material and allyl zinc bromide are subjected to 1,4-Michael addition to form 2-pentyl-3-allyl cyclopentanone; the 2-pentyl-3-allyl cyclopentanone is oxidized by sodium periodate in the presence of a ruthenium trichloride hexahydrate catalyst to synthesize dihydrojasmonic acid; and then the dihydrojasmonic acid is esterified to form the methyl dihydrojasmonate. The raw material of the method is cheap and low in cost; the process is simple and convenient in operation; the reaction conditions are mild and easy to control; the synthesis route is short and the synthesis period is reduced greatly; and the reaction product is single, high in yield (up to 65 to 85 percent), less in environmental pollution, and environmentally-friendly.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a method for synthesizing methyl dihydrojasmonate, in particular to a method for synthesizing methyl dihydrojasmonate by using an organic zinc reagent. Background technique [0002] Methyl dihydrojasmonate is the latest synthesized jasmone-like compound and is a very important spice in the modern perfume industry. Methyl dihydrojasmonate is a colorless to pale yellow liquid with a strong jasmine aroma and a fresh orchid-like fragrance. It volatilizes slowly and gently, and the fragrance lasts for a long time. Its structural formula is as follows: [0003] [0004] Methyl dihydrojasmonate is insoluble in water, but soluble in organic solvents such as ethanol. It can be directly used as a fragrance without preparation to prepare artificial jasmine oil; it can also be used as a synergist for food flavors in fragrance flavors; this fragrance not only has a fresh and eleg...

Claims

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Application Information

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IPC IPC(8): C07C69/716C07C67/08
Inventor 胡雨来冯惠娟黄丹凤徐长明
Owner NORTHWEST NORMAL UNIVERSITY
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