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Method for preparing 2, 4-disubstituted tetrahydropyran compound through hydrogenolysis reaction

A technology of tetrahydropyran compound and tetrahydropyran, applied in the direction of organic chemistry, etc., can solve the problem of low yield

Pending Publication Date: 2022-04-12
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although these routes are easy to get raw materials, but the yield is not high
[0008] In conclusion, the current routes for the synthesis of 2,4-disubstituted tetrahydropyran compounds such as rose oxide have many shortcomings in industrial production, so a new route is developed to synthesize rose oxide with high yield and high selectivity 2,4 -Disubstituted tetrahydropyran compounds are of great significance

Method used

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  • Method for preparing 2, 4-disubstituted tetrahydropyran compound through hydrogenolysis reaction
  • Method for preparing 2, 4-disubstituted tetrahydropyran compound through hydrogenolysis reaction
  • Method for preparing 2, 4-disubstituted tetrahydropyran compound through hydrogenolysis reaction

Examples

Experimental program
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Effect test

Embodiment 1

[0049] Synthesis of compound rose oxide I-1.

[0050] In a pressure-resistant reactor, add raw materials hydroxyrose ether II-1 (1mol, 1equiv, syn / anti is 3.56), hydrogen donor formic acid (5mol, 5equiv), organic phosphonic acid catalyst V-1 at room temperature (0.03mol, 3mol%) and 300mL of dichloromethane, keeping the stirring speed at 800rpm. The temperature program was started, and after the reaction temperature rose to 50° C., the reaction was continued for 4 h, and the reaction was stopped. The reaction was lowered to room temperature, the reaction kettle was opened, and the reaction solution was analyzed by gas-phase internal standard method. The conversion rate of hydroxyrose ether II-1 was 83%, the selectivity was 86%, and the product syn / anti was 3.57. Dichloromethane was recovered from the obtained oil phase under the conditions of 400hPaA and 25°C, and the raffinate was further purified by rectification under the conditions of 20 trays and a reflux ratio of 3 to o...

Embodiment 2

[0052] Synthesis of compound rose oxide I-1.

[0053] In a pressure-resistant reactor, add the raw material hydroxyrose ether II-1 (1mol, 1equiv, syn / anti is 3.56), hydrogen donor Hans ester III-1 in sequence at room temperature (5 mol, 5 equiv), organic phosphonic acid catalyst V-1 (0.03 mol, 3 mol%) and 300 mL of dichloromethane, and keep the stirring speed at 800 rpm. The temperature program was started, and after the reaction temperature rose to 50° C., the reaction was continued for 4 h, and the reaction was stopped. The reaction was lowered to room temperature, the reaction kettle was opened, and the reaction solution was analyzed by gas-phase internal standard method. The conversion rate of hydroxyrose ether II-1 was 97%, the selectivity was 98%, and the product syn / anti was 3.54.

Embodiment 3

[0055] Synthesis of compound rose oxide I-1.

[0056] In a pressure-resistant reactor, add the raw material hydroxyrose ether II-1 (1mol, 1equiv, syn / anti is 3.56), hydrogen donor Hans ester III-2 in sequence at room temperature (5 mol, 5 equiv), organic phosphonic acid catalyst V-1 (0.03 mol, 3 mol%) and 300 mL of dichloromethane, and keep the stirring speed at 800 rpm. The temperature program was started, and after the reaction temperature rose to 50° C., the reaction was continued for 4 h, and the reaction was stopped. The reaction was lowered to room temperature, the reaction kettle was opened, and the reaction solution was analyzed by gas-phase internal standard method. The conversion rate of hydroxyrose ether II-1 was 92%, the selectivity was 91%, and the product syn / anti was 3.55.

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Abstract

The invention provides a method for preparing a 2, 4-disubstituted tetrahydropyran compound through a hydrogenolysis reaction. A 2, 4-disubstituted tetrahydropyran-4-alcohol compound is used as a raw material, under the action of an organic phosphonic acid catalyst, the 2, 4-disubstituted tetrahydropyran-4-alcohol compound reacts with a hydrogen donor in one step to obtain the 2, 4-disubstituted tetrahydropyran-4-alcohol compound, and the reaction has the characteristics of high yield, good selectivity, obvious application value and the like. Under the catalytic system, perfume rose oxide and dihydrorose oxide can be obtained in one step.

Description

technical field [0001] The invention belongs to the technical field of fine chemicals, and in particular relates to a method for preparing 2,4-disubstituted tetrahydropyran compounds through hydrogenolysis. Background technique [0002] Many 2,4-disubstituted tetrahydropyran compounds are widely used in the fields of flavors and seasonings. For example, rose ether, whose chemical name is 2-(2-methyl-1-propenyl)-4-methyltetrahydropyran, is an expensive essence with grassy fragrance and rose fragrance, because of its unique rose fragrance , is widely used in the preparation of fragrant leaves and rose cosmetics. Another example is dihydrorose ether, whose chemical name is 2-(2-methylpropyl)-4-methyltetrahydropyran. This compound is similar to rose ether, with characteristic geranium and rose fragrance, and because of Hydrorose ether is a saturated structure with better stability. [0003] [0004] Although 2,4-disubstituted tetrahydropyran compounds have good properties,...

Claims

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Application Information

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IPC IPC(8): C07D309/04
CPCY02P20/55
Inventor 张德旸张永振蔺海政刘连才姜鹏石森黎源
Owner WANHUA CHEM GRP CO LTD
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