10067-31-9

Upstream product

• 5989-54-8 (-)-(S)-limonene 
• 64-19-7 acetic acid 
• 108-24-7 acetic anhydride 
• 147009-74-3 4S-(-)-9-chloro-1,8-p-menthadiene 
• 10067-33-1 (S)-(-)-p-mentha-1,8⁽¹⁰⁾-dien-9-ol 

Downstream Products

• 25151-81-9 PROSTANOIC ACID 
• 89822-05-9 Acetic acid 2-((S)-3,4-dihydroxy-4-methyl-cyclohexyl)-allyl ester 
• 319449-29-1 (S)-(-)-2-phenylselenyl-p-menth-8⁽¹⁰⁾-ene-1,9-diol 
• 319449-30-4 (S)-(-)-p-mentha-2,8⁽¹⁰⁾-diene-1,9-diol 

Relevant academic research and scientific papers

Regioselective catalytic acetoxylation of limonene

Two efficient strategies for a direct catalytic and regioselective acetoxylation of terpenes are described. Acetoxylated limonene derivatives were synthesized via palladium-catalyzed C-H activation utilizing para-benzoquinone (BQ) as reoxdidation agent and acetic acid as solvent and reactant. Addition of dimethyl sulfoxide (DMSO) to the catalytic system led to highly selective functionalization of the exocyclic double bond of limonene. This catalytic acetoxylation of limonene was further optimized with regard to a more sustainable and environmentally-friendly procedure. On the other hand, the use of an aerobic tandem catalytic system using iron(ii) phthalocyanine (Fe(Pc)) as co-catalyst, which acts as electron transfer mediator (ETM), enabled a highly selective acetoxylation of the endocyclic double bond of limonene with high conversions. Moreover, diacetoxylated products were prepared by a reaction sequence applying the aforementioned catalytic systems.

Short synthesis of vesperal [(S)-10-oxoisopiperitenone], the female sex pheromone of the longhorn beetle (Vesperus xatarti), and of its enantiomer

Vesperal [(S)-10-oxoisopiperitenone, 1], the female sex pheromone of the longhorn beetle (Vesperus xatarti), was synthesized from (R)-limonene (3) in 6% overall yield (6 steps). The non-natural (R)-vesperal was also prepared from (S)-limonene.

Reactions of d-Limonene with t-Butyl Hypochlorite

Investigation of the title reaction under different conditions of temperature, solvents and catalysis has led to its optimisation with respect to the yield of (-)-trans-carvyl chloride (2).Other products formed in the reaction have been identified as 1,2-dichloro-p-menth-8-ene (5), 10-chloro-p-mentha-1,8-diene (6), 2-chloro-p-mentha-1(7)8-diene (10) and 6,10-dichloro-p-mentha-1,8-diene (11).The reaction proceeds almost entirely by electrophilic halogenation with no evidence of competition from a radical mechanism.