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Method for preparing tetrahydroedulan

A technology of dihydro and ionol, which is applied in the field of preparation of tetrahydro-iduran, can solve the problems of difficult post-processing of intermediate products, low yield of final products, environmental pollution and the like

Inactive Publication Date: 2011-09-28
YUNNAN RES INST OF TOBACCO SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In the synthetic methods of edulan spices reported in the literature, some reactions require special reaction raw materials, some reactions must adopt special reaction equipment and certain atmosphere protection, and most of them reflect that they need to be carried out step by step, the reaction cycle is long, and the reaction proceeds The yield of the final product is very low, and a large number of intermediate products are produced during the reaction, which not only causes difficulties in post-processing, but also poses a risk of serious pollution to the environment

Method used

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  • Method for preparing tetrahydroedulan
  • Method for preparing tetrahydroedulan

Examples

Experimental program
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Effect test

Embodiment 1

[0014] Embodiment 1: the preparation of tetrahydroiduran

[0015] Add 60mL of toluene solution containing 10% (mass fraction) dihydro-α-ionol to a reaction kettle with a volume of 150mL, so that the filling rate (volume ratio) of the reaction kettle is about 40%, and then press the total mass of the solution at 0.3 % ratio to add p-toluenesulfonic acid and concentrated sulfuric acid (mass ratio of 1:1). The above mixture was refluxed for 4h. After the reaction was completed, the pH was adjusted to 7 with 5% (mass fraction) sodium carbonate aqueous solution. After the organic layer was separated, it was washed three times with the same volume of water, and the organic layer was dried over anhydrous sodium sulfate. The toluene was distilled off under reduced pressure to obtain the crude product.

[0016] The crude product obtained above was subjected to chromatographic column separation with a mixed solvent of v petroleum ether / v ethyl acetate=90 / 1 to obtain the target tetrah...

Embodiment 2

[0017] Embodiment 2: the preparation of tetrahydroiduran

[0018] Add 90mL of toluene solution containing 20% ​​(mass fraction) of dihydro-α-ionol into a reaction kettle with a volume of 150mL, so that the filling rate (volume ratio) of the reaction kettle is about 60%. % ratio to add p-toluenesulfonic acid and concentrated sulfuric acid (mass ratio of 1:1). The above mixture was refluxed for 8h. After the reaction was completed, the pH was adjusted to 7 with 5% (mass fraction) sodium carbonate aqueous solution. After the organic layer was separated, it was washed three times with the same volume of water, and the organic layer was dried over anhydrous sodium sulfate. The toluene was distilled off under reduced pressure to obtain the crude product.

[0019] The crude product obtained above was subjected to chromatographic column separation with a mixed solvent of v petroleum ether / v ethyl acetate=100 / 1 to obtain the target product tetrahydroiduran. Under the condition that...

Embodiment 3

[0020] Embodiment 3: the preparation of tetrahydroiduran

[0021] Add 75mL of toluene solution containing 15% (mass fraction) dihydro-α-ionol to a reaction kettle with a volume of 150mL, so that the filling rate (volume ratio) of the reaction kettle is about 50%, and then press the total mass of the solution to be 0.4 % ratio to add p-toluenesulfonic acid and concentrated sulfuric acid (mass ratio of 1:1). The above mixture was refluxed for 6h. After the reaction was completed, the pH was adjusted to 7 with 5% (mass fraction) sodium carbonate aqueous solution. After the organic layer was separated, it was washed three times with the same volume of water, and the organic layer was dried over anhydrous sodium sulfate. The toluene was distilled off under reduced pressure to obtain the crude product.

[0022] The crude product obtained above was subjected to chromatographic column separation with a mixed solvent of v petroleum ether / v ethyl acetate=95 / 1 to obtain the target tet...

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Abstract

The invention relates to a method for preparing tetrahydroedulan, which is characterized by comprising the following steps of: adding methylbenzene solution which contains 10 to 20 percent of alpha,2,6,6-tetramethylcyclohexene-1-propan-1-ol serving as a raw material into a reaction kettle to make the fill rate of the reaction kettle 40-60 percent; adding p-toluenesulfonic acid and concentrated sulfuric acid (in a mass ratio of 1:1) which are respectively 0.3 to 0.5 percent of the total amount of solution; refluxing the mixed solution for 4 to 8 hours; after the reaction is finished, regulating the pH to be 7 by using 5 percent aqueous solution of sodium carbonate; separating out an organic layer, washing with water in the same volume for three times, and drying the organic layer by using anhydrous sodium sulfate; distilling under reduced pressure to remove the methylbenzene so as to obtain a crude product; and performing chromatographic column separation on the crude product in a mode of gradient elution through a mixed organic solvent to obtain the target product of tetrahydroedulan. The method has the advantages of simple and readily available raw material, simple operation, high conversion rate of reaction, environmental friendliness, and suitability for batch production.

Description

technical field [0001] The invention belongs to the preparation method of tetrahydroiduran, and relates to the selective catalytic cyclization reaction of unsaturated enol. Background technique [0002] Edulans are benzopyran derivatives that were discovered in the 1970s from Passiflora edulis, Sims. Idulan spices have a strong rose-like aroma, and the aroma characteristics are slightly different with different structures. Although the unique and elegant aroma is a trace aroma component of egg fruit, it is still considered to be the key aroma component of egg fruit. [0003] Idulan spices have a unique and elegant aroma, and are widely found in aroma components such as food, cosmetics, beverages, and cigarettes. Some foreign scholars have carried out research on the preparation method on the synthesis of iduran spices, but mainly focus on such as figure 1 In edulan I-IV (Idulan I-IV), dihydroedulan I-II (dihydro Idulan I-II), oxo-edulan I-II (oxaidulan I-II), and tetrahydr...

Claims

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Application Information

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IPC IPC(8): C07D311/74
Inventor 陈永宽谢冰刘志华王璐刘春波刘巍张承明王保兴
Owner YUNNAN RES INST OF TOBACCO SCI