Octanol-based aroma chemicals, Part 4. A simple synthesis of dihydrojasmone

We have developed a new synthetic method for the preparation of dihydrojasmone via a five‐step synthesis from n‐octanol. Oxidation of n‐octanol gave n‐octanal, which after Mannich reaction and hydrogenation yields 2‐methyl octanal. Knoevenagel condensation of this substituted aldehyde gave 4‐methyld...

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Bibliographic Details
Published in:Flavour and fragrance journal 2007-05, Vol.22 (3), p.214-216
Main Authors: Zope, Dhananjay D., Patnekar, Shridhar G., Kanetkar, Vinod R.
Format: Article
Language:English
Subjects:
2-methyl octanal
4-methyldec-3-enoic acid
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Applied sciences
Chemical industry and chemicals
Chemistry
cyclization
dihydrojasmone
Essential oils, perfumes
Exact sciences and technology
Knoevenagel condensation
n-octanol
octanal
Organic chemistry
Preparations and properties
Washing products. Cosmetics and toiletries. Perfumes
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Summary:We have developed a new synthetic method for the preparation of dihydrojasmone via a five‐step synthesis from n‐octanol. Oxidation of n‐octanol gave n‐octanal, which after Mannich reaction and hydrogenation yields 2‐methyl octanal. Knoevenagel condensation of this substituted aldehyde gave 4‐methyldec‐3‐enoic acid, which on cyclization furnished dihydrojasmone. The process is simple and may be substituted for the existing process of synthesizing dihydrojasmone by the use of 1,4‐dicarbonyl ketones. Copyright © 2007 John Wiley & Sons, Ltd.
ISSN:0882-5734
1099-1026
DOI:10.1002/ffj.1786