Synthesis method of 1, 1, 3, 5-tetramethyl-3-isopropyl hydrindene

A technology of isopropylindane and its synthesis method, which is applied in the fields of chemical instruments and methods, isomerization of hydrocarbons, and carbon compound catalysts, and can solve the problems of low synthesis yield of indane compounds and high difficulty in purification of target products, etc. Achieve the effect of reducing the difficulty of purification, reducing the difficulty of obtaining and increasing the yield

Pending Publication Date: 2020-01-17
TIANMEN DEYUAN CHEM TECH CO LTD
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  • Application Information

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Problems solved by technology

[0005] In order to overcome the above-mentioned deficiencies of the prior art, the present invention proposes a synthetic method of 1,1,3,5-tetramethyl-3-isopropylindane, which solves the problem that the synthetic yield of existing indane compounds is relatively low , and the purification difficulty of the target product is high technical problem, the synthesis reaction steps are as follows:

Method used

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  • Synthesis method of 1, 1, 3, 5-tetramethyl-3-isopropyl hydrindene
  • Synthesis method of 1, 1, 3, 5-tetramethyl-3-isopropyl hydrindene

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Embodiment 1

[0023] A kind of synthetic method of 1,1,3,5-tetramethyl-3-isopropylindane, specifically comprises the following steps:

[0024] S1: Mix 120g of p-cymene, 100g of tert-butyl chloride and 100g of 2,3-dimethyl-1-butene, and then add the mixture dropwise to a tank containing 350g of cyclohexane and 15g of aluminum trichloride. In a reaction flask, stir the reaction, wash with water and alkali to elute the solvent, and rectify and remove p-cymene at 100°C under a pressure of -0.09MPa. , so a large amount of cymene is removed to obtain the crude product of 1,1,3,4,4,6-hexamethyltetrahydronaphthalene;

[0025] S2: Isomerize the crude 1,1,3,4,4,6-hexamethyltetralin, then add 150g of dichloroethane and 35g of aluminum trichloride, stir and heat up to 35°C, and reflux for 1.5 hours ;

[0026] S3: The product after the isomerization reaction is washed with water and alkali to neutrality, and dichloroethane is removed by precipitation, and the 1,1,3,5-tetramethyl-3-isopropylindane afte...

Embodiment 2

[0028] S1: Mix 320g of p-cymene, 165g of tert-butyl chloride and 100g of 2,3-dimethyl-1-butene, and then add the mixture dropwise to a tank containing 400g of cyclohexane and 20g of aluminum trichloride. In a reaction flask, stir the reaction, wash with water and alkali to elute the solvent, and rectify and remove p-cymene at 120°C under a pressure of -0.095MPa to obtain 1,1,3,4,4,6-hexamethyltetra crude hydrogenated naphthalene;

[0029] S2: Isomerize the crude 1,1,3,4,4,6-hexamethyltetralin, then add 240g of dichloroethane and 28g of aluminum trichloride, stir and raise the temperature to 55°C, and reflux for 2 hours ;

[0030] S3: The product after the isomerization reaction is washed with water and alkali to neutrality, and dichloroethane is removed by precipitation, and the 1,1,3,5-tetramethyl-3-isopropylindane after precipitation is Recrystallize the crude product, add 80g of crystallization solvent, raise the temperature to 50°C, lower the temperature to 30°C for 2h a...

Embodiment 3

[0032] S1: Mix 500g of p-cymene, 500g of tert-butyl chloride and 100g of 2,3-dimethyl-1-butene evenly, then add the mixture dropwise to a tank containing 700g of cyclohexane and 25g of aluminum trichloride In a reaction flask, stir the reaction, wash with water and alkali to elute the solvent, and rectify and remove p-cymene at 120°C under a pressure of -0.1MPa to obtain 1,1,3,4,4,6-hexamethyltetra crude hydrogenated naphthalene;

[0033] S2: Isomerize the crude 1,1,3,4,4,6-hexamethyltetralin, then add 300g dichloroethane and 90g aluminum trichloride, stir and heat up to 55°C, and reflux for 2 hours ;

[0034] S3: The product after the isomerization reaction is washed with water and alkali to neutrality, and dichloroethane is removed by precipitation, and the 1,1,3,5-tetramethyl-3-isopropylindane after precipitation is Recrystallize the crude product, add 100g crystallization solvent, raise the temperature to 50°C, lower the temperature to 30°C for 2h at a stirring rate of 2...

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Abstract

The invention relates to a synthetic method of 1, 1, 3, 5-tetramethyl-3-isopropyl hydrindene. The synthetic method specifically comprises the following steps: S1, uniformly mixing p-cymene, chlorotert-butane and 2, 3-dimethyl-1-butene, dropwise adding an obtained mixed solution into a reaction kettle filled with cyclohexane and aluminum trichloride, stirring for reaction, washing with water and alkali for elution, and rectifying to remove p-cymene, so as to obtain a 1, 1, 3, 4, 4, 6-hexamethyltetrahydronaphthalene crude product; S2, transferring the 1, 1, 3, 4, 4, 6-hexamethyl tetrahydronaphthalene crude product obtained in the step S1 into an isomerization kettle, then adding dichloroethane and aluminum trichloride, and carrying out stirring, heating and reflux reaction; S3, washing a product obtained after the isomerization reaction with water and alkali until the product is neutral, desolventizing to remove dichloroethane, transferring an obtained desolventized 1, 1, 3, 5-tetramethyl-3-isopropyl hydrindene crude product into a crystallization kettle, adding a crystallization solvent, and recrystallizing for multiple times to obtain the 1, 1, 3, 5-tetramethyl-3-isopropyl hydrindene. According to the synthetic method of the 1, 1, 3, 5-tetramethyl-3-isopropyl hydrindene, provided by the invention, the yield of a target product is improved, and the purification difficulty is reduced.

Description

technical field [0001] The invention relates to the technical field of synthesis of polycyclic musk intermediates, in particular to a synthesis method of 1,1,3,5-tetramethyl-3-isopropylindane. Background technique [0002] Polycyclic musks have been widely used in the fields of cosmetics, detergents, perfumes and medicines. Because of its stable acid and alkali resistance, it has become one of the most promising synthetic musks. There is also a slight musky aroma after melting; [0003] [0004] Usually the synthetic technique of indane structure has: substituent benzene and olefin form indane (US4877912) under the catalysis of protonic acid or Lewis acid; The preparation method of powder sandalwood musk. According to the above direct synthesis of 1,1,3,5-tetramethyl-3-isopropylindane, firstly, the olefins and alcohols required by the raw materials are difficult to obtain, and secondly, the reaction yield is low, about 20-25%. According to the synthesis of the indane ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C5/29C07C7/14C07C13/465
CPCC07C5/29C07C7/14C07C1/26C07C2602/08C07C2602/10C07C2527/126C07C13/465C07C13/48
Inventor 刘升黎明黎继俭虞军
Owner TIANMEN DEYUAN CHEM TECH CO LTD
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