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Synthetic method of musk tibetene

A Tibetan musk and synthetic method technology, applied in the field of chemical industry, can solve the problems of complex process, low yield, long process, etc., and achieve the effects of low requirements on reaction conditions, simple and efficient synthetic method, and low environmental pollution

Inactive Publication Date: 2014-02-26
SHANGHAI INST OF MEASUREMENT & TESTING TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the complex process, long process and low yield, the output is very small

Method used

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  • Synthetic method of musk tibetene
  • Synthetic method of musk tibetene
  • Synthetic method of musk tibetene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Embodiment 1: the synthetic method of 5-tert-butylthylene

[0019]

[0020] Add three-necked benzene (1.2g, 10mmol), anhydrous ferric chloride (0.1g, 0.6mmol) and dichloromethane (15mL) in sequence in the three-necked flask, and slowly add tert-butanol (0.5mL, 5mmol) di Chloromethane solution (10 mL), keep the temperature below 80°C during the dropwise addition. After the dropwise addition, it was heated to 80° C. to continue the reaction for 2 hours. After cooling, it was quenched with ice water, separated, and the aqueous phase was extracted three times with dichloromethane (15mL). The combined organic phase was washed with saturated brine and anhydrous Na 2 SO 4 dry. Filter and remove solvent under reduced pressure. The residue was distilled under reduced pressure, and the 85-88°C fraction (1.33kPa) was collected to obtain 5-tert-butylthylene (1.26g, 72.0%).

Embodiment 2

[0021] Example 2: Synthesis of Tibetan musk from 5-tert-butylthylene

[0022]

[0023] Cuprous chloride (0.1g, 1.0mmol), anhydrous acetic acid (1.0mL), 5-tert-butylthylene (1.76g, 10.0mmol) and carbon tetrachloride (30mL) were added to the flask, and the Fuming nitric acid (1.2 mL) was slowly added dropwise, and after 2 hours of reaction, the temperature was slowly raised to room temperature and the reaction was continued for 6 hours. After the reaction is completed, dilute with ice water, neutralize, and filter, and the filter cake is washed with water and dried to obtain the crude product of Tibetan musk.

[0024] Characterization data: m.p.134-136°C; 1 H NMR (400MHz, CDCl 3 )δ2.41(6H,s),2.20(3H,s),1.33(9H,s); 13 C NMR (100MHz, CDCl 3 )δ151.2, 134.7, 134.5, 133.6, 29.3, 27.9, 15.9, 14.1; ESI-MS, m / z=267.5 ([M+H] + ).

Embodiment 3

[0025] Embodiment 3: the recrystallization of Tibetan musk synthetic crude product

[0026] The crude product of Tibetan musk (3.0g) was heated to 80°C with ethanol (20mL) as a solvent, filtered while hot after dissolution, slowly cooled to 40-45°C, kept for 1 hour, and filtered. Repeat 2 times to obtain pure Tibetan musk with a purity greater than 99%.

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Abstract

The invention discloses a method for efficient synthesis of musk tibetene from 1, 2, 3-trimethylbenzene. The method includes: firstly letting 1, 2, 3-trimethylbenzene undergo Friedel-Crafts alkylation reaction to generate 5-tertbutyl-1, 2, 3-trimethylbenzene, then under catalysis of Lewis acid, making the 5-tertbutyl-1, 2, 3-trimethylbenzene react with nitric acid to generate musk tibetene, then carrying out follow-up technological treatment by subjecting the reaction mixture to dilution, neutralization and filtration, and then conducting separation by recrystallization, thus obtaining a pure product. The synthetic method provided by the invention is simple and efficient, has low requirement for raw materials, and has no need for ultra-high purity 1, 2, 3-trimethylbenzene. The requirements for reaction conditions are low, and by means of simple follow-up treatment steps, the high purity musk tibetene can be obtained. In addition, compared with the prior art, the method provided by the invention causes much lower environmental pollution.

Description

technical field [0001] The invention belongs to the technical field of chemical industry, and relates to a method for synthesizing Tibetan musk by using pylene as a raw material. Background technique [0002] Musk Tibetan (Musk Tibetan) is also known as trimethylbenzene musk, and its chemical name is 5-tert-butyl-1,2,3-trimethyl-4,6-dinitrobenzene. It is a relatively expensive nitro musk. It has a sweet and soft natural musk animal aroma, similar to ketone musk, with a long-lasting and powerful fragrance, which is stable and does not change color when exposed to light. It can be used as an animal-scented fragrance and fixative in various daily chemical essences that require a musky fragrance. It can play a very good rounding and modifying role in some sweet and heavy fragrance types. [0003] In addition, studies have shown that Tibetan musk has the characteristics of low polarity, strong lipophilicity and easy bioaccumulation. Toxicology experiments show that it has pote...

Claims

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Application Information

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IPC IPC(8): C07C205/06C07C201/08
Inventor 李杰王虎陈鹰
Owner SHANGHAI INST OF MEASUREMENT & TESTING TECH
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