86414-33-7

Upstream product

• 67214-54-4 (R)-citronellyl tosylate 
• 35026-81-4 (2S)-methylbuthyl-1-magnesium bromide 
• 10422-35-2 1-bromo-2-methyl-butane 
• 41144-01-8 (S)-3,7-dimethyl-6-octenyl tosylate 

Downstream Products

• 87106-39-6 4,8-dimethyldecanal dimethylacetal 
• 85880-36-0 (4S,8S)-(+)-4,8-trimethyldecanal 

Relevant academic research and scientific papers

PRODUCTION METHOD OF 4,8-DIMETHYLDECANAL

PROBLEM TO BE SOLVED: To provide a method of producing a mixture of (4R,8S)-4,8-dimethyldecanal and (4R,8R)-4,8-dimethyldecanal effective as pheromones for rust-red flour beetles and confused flour beetles, practically in a high yield through a small number of steps. SOLUTION: A method of producing a mixture of (4R,8S)-4,8-dimethyldecanal and (4R,8R)-4,8-dimethyldecanal includes a first step of tosylating (S)-citronellol to obtain a tosylate, a second step of reacting the tosylate with a Grignard reagent to obtain an alkene, a third step of epoxidating the alkene to obtain an epoxide, and a fourth step of cleaving the epoxide with a periodic acid to obtain 4,8-dimethyldecanal. COPYRIGHT: (C)2015,JPOandINPIT

OZONOLYSIS OF ALKENES AND REACTIONS OF POLYFUNCTIONAL COMPOUNDS. XLVI. SYNTHESIS OF (4S,8S)-4,8-DIMETHYLDECANAL AND ITS DIMETHYL ACETAL

From accessible chiral structural blocks, namely, (R)-methyl-citronellate and (S)-2-methyl-1-butanol, (6S,10S)-2,6,10-trimethyl-2-dodecene was synthesized.The ozonolysis of this gave (4S,8S)-4,8-dimethyldecanal, one of the stereoisomers of the aggregation pheromone of the meal worms Tribolium confusium and T. castaneum, and its dimethyl acetal.