ARS | Publication request: Facile biphasic deprotection of aldehyde dimethylhydrazones with aqueous hydrochloric acid

Submitted to: Letters in Organic Chemistry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: July 12, 2007
Publication Date: September 15, 2007
Citation: Petroski, R.J. 2007. Facile biphasic deprotection of aldehyde dimethylhydrazones with aqueous hydrochloric acid. Letters in Organic Chemistry. 4:452-455.

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 how to overcome a major roadblock in the synthetic organic chemistry required to answer the request of our customers and stakeholders for a shorter, faster, and more cost-effective synthesis of sap beetle pheromones. These results are important to scientists, especially those in industry, because synthetic pathways must be capable of scale-up in order to be viable for commercial production.

Technical Abstract: Deprotection of aldehyde dimethylhydrazones was accomplished by stirring a biphasic mixture of the aldehyde dimethylhydrazone, 1M hydrochloric acid, and petroleum ether at room temperature for three to seven hours. The reaction time for the deprotection of aldehyde dimethylhydrazones varied with the structure of the aldehyde. The method even works with difficult to deprotect alpha,beta-unsaturated- and diene-aldehyde dimethylhydrazones. Isolated yields ranged from 85% to 97%.