Submitted to: Synthetic Communications
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 12/29/2005
Publication Date: 6/23/2006
Citation: Petroski, R.J. 2006. Preparation and deprotection of aldehyde dimethylhydrazones. Synthetic Communications. 36(12):1727-1734.
Interpretive Summary: There is a continuing need to develop more efficient pest and weed control strategies. The use of insect pheromones has become an important part of the process because of cost savings and selectivity. Difficulties occur when the chemical synthesis of the pheromone substances is lengthy or expensive. This paper describes a new efficient method of preparing key intermediates in synthetic pathways leading to certain insect pheromones. These results are important to scientists, especially those in industry, because synthetic pathways must be capable of cost-effective scale-up in order to be viable for commercial production.
Technical Abstract: Aldehydes were conveniently protected as dimethylhydrazones by stirring a mixture of the aldehyde, N,N-dimethylhydrazine, anhydrous magnesium sulfate, and dichloromethane at room temperature. Azeotropic removal of water, formed during the course of the reaction, was not required because anhydrous magnesium sulfate functions as a water scavenger. Deprotection of aldehyde dimethylhydrazones was accomplished by stirring a mixture of the aldehyde dimethylhydrazone and aqueous glyoxylic acid at room temperature. The reaction time for the preparation and deprotection of aldehyde dimethylhydrazones varied with the structure of the aldehyde.