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A facile method for monoacetylation of symmetrical diols: application to the total synthesis of Z-8-dodecenyl acetate, the sex attractant of the oriental fruit moth

✍ Scribed by James H. Babler; Michael J. Coghlan

Publisher
Elsevier Science
Year
1979
Tongue
French
Weight
240 KB
Volume
20
Category
Article
ISSN
0040-4039

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✦ Synopsis

Sumnary: By the use of continuous extraction of the reaction mixture with a suitable nonr)olar solvent, several symmetrical 1" and 2' diols were converted in hiqh yield to the corresponding monoacetate derivative in aqueous acetic acid solution. A recent review1 mentions that monoprotected derivatives (e.g., 2_) of the inexpensive symnetrical diols of general structure 1 are attractive intermediates in synthesizing sex iheromones (e.g., 3) of Lepidoptera.2 The author also points out that preparing such comlounds in solution is complicated by the difficulty in separating the mixtures of dipro-tected, monoprotected, and unprotected products formed. To solve this problem, C. C. Leznoff and coworkers have developed1 the use of insoluble polymer supports.

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Synthesis and pheromonal properties of (
Synthesis and pheromonal properties of (Z)-7,7-difluoro-8-dodecenyl acetate, a difluoro derivative of the sex pheromone of the oriental fruit moth
✍ Marek Masnyk; Josef Fried; Wendell Roelofs πŸ“‚ Article πŸ“… 1989 πŸ› Elsevier Science 🌐 French βš– 193 KB

A synthesis of allylic difluorides is described, exemplified by the preparation of the title compound, which was shown to elicit the biological responses characteristic of (Z)-8-dodecenyl acetate, the pheromone of the Oriental fruit moth. It is concluded that the geometry of the double bond rather t