79861-69-1

Upstream product

• 917-64-6 methyl magnesium iodide 
• 79861-68-0 2-(4'-oxo-Δ^1',2'-cyclohexenyl)-6,10-dimethyl-5,9-undecadiene 
• 79861-65-7 1-(p-methoxyphenyl)-5,9-dimethyl-4,8-decadien-1-ol 
• 18445-88-0 (E)-5,9-dimethyldeca-4,8-dienal 
• 79861-66-8 1-(p-methoxyphenyl)-5,9-dimethyl-4,8-decadien-1-one 
• 79861-67-9 2-(p-methoxyphenyl)-6,10-dimethyl-1,5,9-undecatriene 

Downstream Products

• 70206-74-5 E-2,6-dimethyl-10-(4′-methyl-1′,3′-cyclohexadienyl)-2,6-undecadiene 

Relevant academic research and scientific papers

Synthesis of three putative kairomones of the beech leaf-mining weevil Orchestes fagi (L.)

The beech leaf-mining weevil, Orchestes fagi (L.), also known as the beech flea weevil, is a common and widespread pest of beech, Fagus sylvatica L., in its native Europe. It now appears to be well established in Nova Scotia, Canada. We report a novel synthesis of 9-geranyl-p-cymene and syntheses of 9-geranyl-α-terpinene and 1,1-dimethyl-3-methylene-2-vinylcyclohexane, making partial use of known methods. All three of these compounds are found in beech leaf volatiles and/or wood and are putative kairomones of the beech leaf-mining weevil.

Synthesis of 2-(4'-Methyl-1',3'-cyclohexadienyl)-6,10-dimethyl-5,9-undecadiene (9-Geranyl-α-terpinene)

5,5-Dimethyl-4,8-decadienal (II) on Grignard reaction with p-anisylmagnesium bromide yields the alcohol (III) which on oxidation followed by Wittig reaction with methylenetriphenylphosphorane affords the undecatriene (V).V on lithium/liquid ammonia reduction and subsequent mild hydrolysis with oxalic acid gives 2-(4'-oxo-Δ1',2'-cyclohexenyl)-6,10-dimethyl-5,9-undecadiene (VI).VI on Grignard reaction with methylmagnesium iodide yields VII which on dehydration with phosphorusoxychloride in pyridine furnishes the title compound (I).