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3-methyl-octahydro-cycloheptatriene oxapicene-2-ketone and preparation method thereof

A technology of cycloheptatriene and cycloheptanone, which is applied in the field of 3-methyl-octahydrocycloheptatrien-2-one and its preparation, can solve the complicated and troublesome synthesis method and has no industrial production value and other issues, to achieve the effect of cheap raw materials, low cost, and easy availability of raw materials

Inactive Publication Date: 2010-07-14
SHANGHAI INST OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Since the synthesis method of lactol in the early stage is cumbersome and troublesome, and the oxidant uses PCC, it does not have actual industrial production value

Method used

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  • 3-methyl-octahydro-cycloheptatriene oxapicene-2-ketone and preparation method thereof
  • 3-methyl-octahydro-cycloheptatriene oxapicene-2-ketone and preparation method thereof
  • 3-methyl-octahydro-cycloheptatriene oxapicene-2-ketone and preparation method thereof

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Experimental program
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preparation example Construction

[0050] A preparation method of 3-methyl-octahydrocycloheptatrien-2-one, comprising the following preparation steps:

[0051] (1), cycloheptanone and pyrrolidine are added in solvent, with the method for acid catalysis, carry out dehydration reaction, obtain the cycloheptylpyrrole enamine of structural general formula (II);

[0052] (2), cycloheptylpyrrole enamine and methacrylic acid ester with the general structure formula (II) are heated to reflux in a solvent to carry out michael addition reaction, and then the reaction mixture is hydrolyzed with an acid treatment, heated to reflux, and the pyrrolylamine group is removed, Bare ketone group; Reaction obtains the ester derivative of the cycloheptanone of structural formula (III), namely 2-methyl propionate-cycloheptanone;

[0053] (3), 2-methylpropionate-cycloheptanone with the general structural formula (III) is added in the autoclave, a solvent and a hydrogenation catalyst are added; hydrogen at a certain pressure is charge...

Embodiment 1

[0058] Preparation of 3-methyl-octahydrocycloheptatrien-2-one

[0059] (1), the preparation of cycloheptyl pyrrole enamine

[0060] In a 500mL three-necked flask equipped with a thermometer and an oil-water separator, add 58g of cycloheptanone, 70mL of toluene, 63g of pyrrolidine, and 1g of p-toluenesulfonic acid. The reaction system was heated under reflux for 4 hours. When 9.36 g of water was obtained, the reaction was stopped, cooled to room temperature, 1.1 g of sodium acetate was added, and the reaction solution was filtered. The filtrate was evaporated to remove the solvent under reduced pressure. 57g of the fraction at 135-146°C / 133pa is the product with a yield of 66% and a purity of 91% by GC analysis.

[0061] (2), the preparation of 2-methylpropionate-cycloheptanone

[0062] Add 53g of cycloheptylpyrrolene amine and 100mL of methanol into a 250mL three-necked flask, heat to reflux, add 40g of methyl methacrylate dropwise within 1h, continue to reflux for 3h after ...

Embodiment 2

[0068] Preparation of 3-methyl-octahydrocycloheptatrien-2-one

[0069] (1), the preparation of cycloheptyl pyrrole enamine

[0070] In a 500mL three-necked flask equipped with a thermometer and an oil-water separator, add 58g of cycloheptanone, 70mL of cyclohexane, 63g of pyrrolidine, and 1g of p-toluenesulfonic acid. The reaction system was heated under reflux for 5 hours. When 9.36 g of water was obtained, the reaction was stopped, cooled to room temperature, 1.2 g of sodium acetate was added, and the reaction solution was filtered. The filtrate was evaporated to remove the solvent under reduced pressure. 60g of the fraction at 140-1148°C / 133pa is the product with a yield of 70% and a purity of 92% by GC analysis.

[0071] (2), the preparation of 2-methylpropionate-cycloheptanone

[0072] Add 53g of cycloheptylpyrrolene amine and 100mL of ethanol to a 250mL three-necked flask, heat to reflux, add 40g of methyl methacrylate dropwise within 1h, continue to reflux for 3h afte...

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Abstract

The invention discloses 3-methyl-octahydro-cycloheptatriene oxapicene-2-ketone and a preparation method thereof. The preparation method of the 3-methyl-octahydro-cycloheptatriene oxapicene-2-ketone mainly comprises the steps of the preparation of cycloheptyl pyrrole enamine, the preparation of 2-methyl ester-cycloheptane ketone, the preparation of methyl ester-cycloheptane alcohol, the preparation of 3-methyl-octahydro cycloheptatriene oxapicene and the like. The preparation method of the 3-methyl-octahydro-cycloheptatriene oxapicene-2-ketone has the advantages of low cost, easy implementation of reaction conditions, high reaction yield and stable product quality, and is convenient for industrialized production. The 3-methyl-octahydro-cycloheptatriene oxapicene-2-ketone prepared through the invention has tonka-bean smell and is suitable for preparing tonka-bean lactone essences.

Description

technical field [0001] The invention relates to 3-methyl-octahydrocycloheptatrienopyran-2-one with general structural formula (I) and a preparation method thereof. [0002] Background technique [0003] Lactone fragrances are the class with the fewest members in the fragrance family, and they rarely exist in nature. Lactones and esters have similar aroma characteristics, that is, they all have outstanding fruity aroma, and can be widely used in the preparation of food flavors and daily flavors, and as intermediates and polymers for synthetic fragrances, drugs and pesticides and solvents for copolymers, etc. Coumarin is a very well-known bicyclic lactone spice. It has a special coumarinous smell. However, due to its liver toxicity, its use in food flavors has been restricted. Therefore, it is urgent to develop a substitute compound for coumarin. [0004] T.V.RajanBabu and William etc. have reported a kind of synthetic structural general formula in. J.Am.Chem.Soc, 1994,11...

Claims

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Application Information

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IPC IPC(8): C07D311/94A23L1/226A23L27/20
Inventor 何锡敏潘仙华王晓科欧文华刘烽
Owner SHANGHAI INST OF TECH
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