Author
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Petroski, Richard |
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Submitted to: Synthetic Communications
Publication Type: Peer Reviewed Journal Publication Acceptance Date: 1/27/2001 Publication Date: N/A Citation: N/A Interpretive Summary: Due to customer concerns about the use of broad-spectrum pesticides and their effect on the environment, we are developing pest control strategies requiring the use of less pesticide. Insect pests produce chemical substances, termed pheromones, that selectively attract members of its own species. We can use pheromone-baited traps in fields to monitor for the presence and numbers of specific insect pests and thus precisely time the use of pesticide sprays. Commercialization of pheromone baits has been impeded by the lack of robust synthetic pathways leading to the compounds. We report the facile synthesis of two compounds that can serve as useful synthetic intermediates to a variety of target compounds. Our research results facilitate the cost- effective use of pheromones in agriculture. Technical Abstract: 2-Methyl-1,3-dioxolane-2-ethanol was prepared in 90% isolated yield from 4-hydroxy-2-butanone and ethylene glycol using a weak acid catalyst and ethyl acetate as the reaction solvent. 2-(2- Bromoethyl)-2-methyl-1,3-dioxolane was prepared in 75% isolated yield by bromination of 2-methyl-1,3-dioxolane-2-ethanol with dibromotriphenylphosphorane, which was prepared in situ by titrating triphenylphosphine with bromine at an ice-ethanol bath temperature. The target compounds are useful intermediates for the synthesis of insect pheromones and natural products. |
