90294-01-2

Upstream product

• 90294-03-4 2,2-dimethyl-3-(2-methyl-2-hydroxypropyl)-cis-cyclopropane-1-acetaldehyde 
• 72367-61-4 2,2-Dimethyl-3-(2-oxopropyl)-cis-cyclopropane-1-acetaldehyde dimethylacetal 
• 26946-58-7 [(1R,3S)-3-(2-Hydroxy-2-methyl-propyl)-2,2-dimethyl-cyclopropyl]-acetic acid methyl ester 
• 26946-57-6 [(1R,3S)-3-(2-Hydroxy-2-methyl-propyl)-2,2-dimethyl-cyclopropyl]-acetic acid 
• 90294-02-3 2,2-Dimethyl-3-(2-hydroxy-2-methylpropyl)-cis-cyclopropane-1-acetaldehyde dimethylacetal 
• 90365-32-5 Methyl (+)-cis-homochrysanthemate 
• 13826-35-2 3-Phenoxybenzyl alcohol 

Relevant academic research and scientific papers

Synthesis of Methyl (+)-cis-Chrysanthemate and (+)-cis-Homochrysanthemate from (+)-3-Carene

Synthesis of (+)-dihydrochrysanthemolactone (III) and methyl (+)-cis-homochrysanthemate (IV) has been achieved via a common intermediate, viz. 2,2-dimethyl-3-(2-hydroxy-2-methylpropyl)-cis-cyclopropane-1-acetaldehyde (V), prepared from (+)-3-carene.The dimethyl acetal (VII), obtainable from V, on reacting with CH3MgI, affords the alcohol (VII) from which the aldehyde (XI) is regenerated and subjected to self-aldol condensation.Oxidation of aldol gives a mixture of acids (XI) and (XIV), the methyl esters of which on LAM reduction affords a mixture of diols (VI) and (XV).Oxidation of diols yields a mixture of lactone (III) and the acid (XIV).Oxidation of IX followed by esterification affords XIV, which on dehydration yields IV and the double bond isomer (XIII).Transesterification of IV with 3-phenoxybenzyl alcohol gives the ester (XVI).Oxidation of VI by KMnO4 yields hydroxy acid (XI), from which methyl chrysanthemate (I) has been obtained.