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Method for synthesizing musk tonalide

A technique for exhaling musk and intermediates, which is applied in the synthesis field of exhaling musk, and achieves the effects of high yield, high yield and less side reactions

Inactive Publication Date: 2010-12-22
上海力智生化科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Commonly used solvents are: halogenated alkanes, such as dichloroethane (J.Org.Chem.1963, 28, 2248), etc., which are more toxic; nitrobenzene (FR1392804), the disadvantage is that the boiling point is high, and separation and recovery are difficult; Saturated alkanes and saturated cyclic alkanes (EP 561447), because the products are easy to form complexes with Lewis acids and are difficult to dissolve in low-polar alkanes, they often precipitate out, resulting in complex reactions

Method used

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  • Method for synthesizing musk tonalide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Add 50g of benzene and 50g of cyclohexane, 10g of anhydrous aluminum trichloride and 2g of concentrated sulfuric acid into a 500mL three-necked flask, add dropwise 108g (0.8mol) of p-cymene, 20g (0.25mol) of 2,3- For the mixture of dimethyl-1-butene and 28g (0.3mol) tert-butyl chloride, the reaction temperature should not exceed 35°C. Continue to react for 0.5-1h after dripping. The reaction solution was poured into ice water. The aqueous phase was separated, and the organic phase was washed with 10% sodium carbonate solution until neutral, and dried. The solvent was recovered and then distilled under reduced pressure to obtain 42 g (yield 78%) of HMT. The product can be recrystallized from ethanol.

Embodiment 2

[0026] Add 100mL of chlorobenzene, 10g of anhydrous aluminum trichloride and 2g of polyphosphoric acid into a 500mL three-necked bottle, stir vigorously and mix evenly, then add dropwise 108g (0.8mol) of p-cymene, 20g (0.25mol) of 2,3-bis A mixed solution of methyl-1-butene and 28g (0.3mol) of tert-butyl chloride, the reaction temperature is controlled to be 15-20°C. Continue to react for 0.5-1h after dripping. The reaction solution was poured into ice water. The aqueous phase was separated, and the organic phase was washed with 10% sodium carbonate solution until neutral, and dried. The solvent was recovered and then distilled under reduced pressure to obtain 38 g (yield 70%) of HMT.

Embodiment 3

[0028] Add 250mL methyl tert-butyl ether and 160g (1.2mol) AlCl to the 1000mL three-necked bottle 3 Slowly add 94g (1.2mol) of acetyl chloride below 20°C, then dropwise add 225g (1mol) of HMT in methyl tert-butyl ether solution, and continue the reaction for 2h after the dropwise addition. Then the reactant was poured into ice water, the organic layer was separated, the aqueous phase was extracted with methyl tert-butyl ether (3×50 mL), and the organic phase was washed with saturated sodium bicarbonate until neutral. After drying, recovering the solvent and distilling under reduced pressure, the fraction at 140-145° C. / 3 mmHg is collected. The yield of the product AHMT is nearly quantitative, and the purity is ≥98.5%. mp55.5~56.8℃, 1 H NMR (400MHz, CDCl 3 )δ: 7.65 (s, 1H), 7.21 (s, 1H), 2.62 (s, 3H), 2.49 (s, 3H), 1.93-0.98 (m, 18H) ppm.

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Abstract

The invention pertains to the field of chemical technology, particularly relates to a method for synthesizing musk tonalide. The method adopts cymene as raw material to cyclize with olefin under the catalysis of mixed Lewis acid, and then through Friedel-Crafts acylation reaction in ether solvent to achieve musk tonalide with purity greater than or equal to 98 percent by nearly 85-percent total yield. The invention improves the compositions of catalyst to improve the selectivity and the yield of cyclization, and optimizes the condition of Friedel-Crafts acylation reaction by screening solvent. Compared with the prior art, the method is characterized in mild condition, simple operation, high purity, high yield of product, etc.

Description

technical field [0001] The invention belongs to the technical field of chemical industry, and in particular relates to a method for synthesizing exhaled musk. Background technique [0002] Tonalide is a synthetic musk with tetralin structure. It has excellent fragrance quality, elegant fragrance, long-lasting fragrance, acid and alkali resistance, no discoloration under natural light, strong diffusion power, and no stimulation to human skin. It has good compatibility with other fragrances and is an ideal fragrance raw material. It is widely used in the fields of cosmetics, perfume, tobacco, essence and medicine, and has become one of the most promising synthetic musk products. [0003] The chemical name of Tuna musk is 7-acetyl-1,1,3,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene (abbreviated as AHMT), usually composed of intermediate 1, 1,3,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene (referred to as HMT) and acetylation reagents such as acetyl chloride or acetic anhydr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/792C07C45/61
Inventor 郑伟朱红
Owner 上海力智生化科技有限公司
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