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A convenient preparative method of oxo‐dimethylallyl compounds from carboxylic acid derivatives
Author(s) -
Inaba Teruhiko,
Aoki Hideyo,
Watanabe Shoji,
Sakamoto Masami,
Fujita Tsutomu
Publication year - 1991
Publication title -
journal of chemical technology and biotechnology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.64
H-Index - 117
eISSN - 1097-4660
pISSN - 0268-2575
DOI - 10.1002/jctb.280520312
Subject(s) - yield (engineering) , chemistry , reagent , carboxylic acid , chloride , thermal decomposition , allylic rearrangement , organic chemistry , decomposition , grignard reagent , acetyl chloride , dehydration , grignard reaction , medicinal chemistry , reaction conditions , catalysis , biochemistry , materials science , metallurgy
Various oxo‐dimethylallyl compounds were prepared from intermediates which are obtained by the reaction of allylic Grignard reagents with carboxylic acid derivatives. For example, the reaction of prenylmagnesium chloride with ethyl hexanoate gave 3,3–dimethyl‐4–prenyl‐1‐nonen‐4–ol (1) in 92% yield. The thermolysis of 1 at the temperature of 693 K gave 2–methyl‐2–decen‐5–one (2) in 81% yield. Furthermore, 3,3–dimethyl‐1‐alken‐4–ones (E) were prepared by the methylation of 1‐alken‐4‐ones (C), which are obtained by the reaction of allylmagnesium chloride with carboxylic acids (A).