23359-01-5Relevant academic research and scientific papers
Facile Synthesis of Racemic 3-Acetoxy-2,6-dimethyl-1,5-heptadiene, the Sex Pheromone of the Comstock Mealybug
Skatteboel, Lars,Stenstroem, Yngve
, p. 93 - 96 (2007/10/02)
A three step synthesis of 3-acetoxy-2,6-dimethyl-1,5-heptadiene is described.Starting from methyl chloroacetate and methyl acrylate, trans- and cis-dimethyl 1,2-cyclopropanedicarboxylate have been prepared.The isomers were treated with methyllithium or methylmagnesium iodide to give the corresponding diols in high yields.Heating the trans diol in a mixture of acetic acid and acetic anhydride at 80 deg C gave the title compound in an overall yield of 50percent based on methyl chloroacetate.The corresponding cis diol gave, under the same conditions, 2,2,4,4-tetramethyl-3-oxabicyclohexane as the only product.
