Preparation method of 6-isopropenyl-3-methyl-9-decenyl acetate and intermediates thereof

Through the nucleophilic substitution reaction of 2-methyl-2,6-heptanede compound and 3-methylpentyl nucleophilic reagent, combined with the deprotection and acetylation steps, 6-isopropenyl-3-methyl-9-decene acetate was successfully prepared, solving the problems of low safety and yield in the prior art, and achieving efficient industrial preparation.

CN113912494BActive Publication Date: 2025-05-13SHIN ETSU CHEMICAL CO LTD
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Patent Information

Application Number
CN202110778909.X
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Priority Date
2021-01-28
Filing Date
2021-07-09
Publication Date
2025-05-13
Estimated Expiration
2041-07-09

AI Technical Summary

Technical Problem

The prior art is difficult to efficiently and safely prepare sufficient amounts of 6-isopropenyl-3-methyl-9-decene acetate, and there are problems of using toxic, explosive reagents and low yields, making it difficult to use in industrial use.

Method used

The nucleophilic substitution reaction was carried out with 2-methyl-2,6-heptanede compound and 3-methylpentyl nucleophilic reagent to form a protected 6-isopropenyl-3-methyl-9-decene compound, and 6-isopropenyl-3-methyl-9-decene acetate was prepared by deprotection and acetylation steps, avoiding oxidation reactions and improving safety and yield.

Benefits of technology

It has achieved efficient and safe preparation of 6-isopropenyl-3-methyl-9-decene acetate, which is suitable for biological or agricultural activity testing and applications, and has solved the difficulties in industrial preparation.

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Abstract

The present invention provides a method for preparing 6-isopropenyl-3-methyl-9-decenyl acetate (5), wherein Ac represents an acetyl group, and the method comprises the following steps: subjecting a 2-methyl-2,6-heptadiene compound (1) having a leaving group X at position 1 to a nucleophilic substitution reaction with a 3-methylpentyl nucleophile (2) having a protected hydroxyl group at position 5 to form a 6-isopropenyl-3-methyl-9-decene compound (3) having a protected hydroxyl group at position 1; subjecting the 6-isopropenyl-3-methyl-9-decene compound (3) having a protected hydroxyl group at position 1 to a deprotection reaction to form 6-isopropenyl-3-methyl-9-decenol (4); and acetylation of the 6-isopropenyl-3-methyl-9-decenol (4) to form 6-isopropenyl-3-methyl-9-decenyl acetate (5).
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