5258-00-4

Upstream product

• 1134-95-8 2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-yl acetate 
• 2102-58-1 (+)-trans-carveol 
• 108-24-7 acetic anhydride 
• 99-49-0 Carvone 
• 1253216-40-8 (5S)-2-methyl-5-(1-methylvinyl)-2-cyclohexen-1-ol 
• 581-55-5 benzylidene 1,1-diacetate 
• 5989-54-8 (-)-(S)-limonene 
• 1197-06-4 cis-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-ol 
• 75-36-5 acetyl chloride 
• 80-56-8 rac-α-pinene 
• 64-19-7 acetic acid 
• 557-34-6 zinc diacetate 
• 30808-80-1 trans-6-chloro-p-mentha-1,8-diene 
• 5989-27-5 D-limonene 

Downstream Products

• 2102-58-1 (+)-trans-carveol 
• 344559-89-3 3-(5-Isopropenyl-2-methyl-2-cyclohexen-1-yl)-3-methyl-2-butanon 
• 344560-06-1 1-(5-Isopropenyl-2-methyl-2-cyclohexen-1-yl)-3-methyl-2-butanon 
• 88835-04-5 2-(5-Isopropenyl-2-methyl-2-cyclohexen-1-yl)-3-pentanon 
• 344443-62-5 1-(5-Isopropenyl-2-methyl-2-cyclohexen-1-yl)-3,3-dimethyl-2-butanon 
• 344438-52-4 2-(5-Isopropenyl-2-methyl-2-cyclohexen-1-yl)-2,4-dimethyl-3-pentanon 
• 138-86-3 limonene. 
• 99-48-9 (4R,6R)-carveol 
• 76704-28-4 (4S,6S)-6-Acetoxy-4-isopropenyl-1-methylcyclohexene 
• 88846-55-3 2-(5-Isopropenyl-2-methyl-2-cyclohexen-1-yl)-1-cyclopentanon 
• 88835-05-6 2-(5-Isopropenyl-2-methyl-2-cyclohexen-1-yl)-1-cyclohexanon 
• 57022-47-6 (4S,6S)-4-Isopropenyl-6-methoxy-1-methyl-cyclohexene 

Relevant academic research and scientific papers

A further step to sustainable palladium catalyzed oxidation: Allylic oxidation of alkenes in green solvents

The palladium catalyzed oxidation of alkenes with molecular oxygen is a synthetically important reaction which employs palladium catalysts in solution; therefore, a solvent plays a critical role for the process. In this study, we have tested several green solvents as a reaction medium for the allylic oxidation of a series of alkenes. Dimethylcarbonate, methyl isobutyl ketone, and propylene carbonate, solvents with impressive sustainability ranks and very scarcely exploited in palladium catalyzed oxidations, were proved to be excellent alternatives for the solvents conventionally employed in these processes, such as acetic acid. Palladium acetate alone or in the combination with p-benzoquinone efficiently operates as the catalyst for the oxidation of alkenes by dioxygen under 5–10 atm. For most substrates, the systems in green solvents showed better selectivity for allylic oxidation products as compared to pure acetic acid; moreover, the reactions in propylene carbonate solutions occurred even faster than in acetic acid.

Formyloxyacetoxyphenylmethane and 1,1-diacylals as versatile O-formylating and O-acylating reagents for alcohols

Formyloxyacetoxyphenylmethane, symmetric 1,1-diacylals and mixed 1-pivaloxy-1-acyloxy-1-phenylmethanes have been used as moisture stable O-formylating and O-acylating reagents for primary and secondary alcohols, allylic alcohols and phenols under solvent/catalyst free conditions to afford their corresponding esters in good yield.

Method of alcoholization of D-carvone and separation of enantiomer

The invention discloses a method of reduction alcoholization of D-carvone and resolution of an enantiomer by biocatalysis. The D-carvone is taken as a raw material and subjected to reduction with sodium borohydride to obtain a compound II, the compound II is subjected to enzymatic kinetic resolution reaction to obtain a compound III and a compound IV, or the compound II is subjected to dynamic kinetic resolution to obtain the compound III of which the yield is higher than 90%, and a compound V can be obtained by hydrolyzing the compound III. The method further changes a prochiral ketone group in the D-carvone into a chiral hydroxyl center and carries out further resolution; and the method has the characteristics of simplicity of operation, high yield of product, good optical purity and the like.

Enantiomeric differentiation of oxygenated p-menthane derivatives by 13C NMR using Yb(hfc)3

The 13C NMR behaviour of 21 p-menthanic terpene bearing an oxygenated function (alcohol, ketone, acetate) was examined in the presence of a chiral lanthanide shift reagent (Yb(hfc)3). For each monocyclic compound, we measured the lanthanide-induced shift (LIS) on the signals of the carbons and the splitting of signals allowing the enantiomeric differentiation. Some general features were found about their LIS behaviour: experimental data establishing distinct patterns for carvomenthone-like compounds and menthone-like compounds. The enantiomeric splitting was observed for the majority of signals in the spectrum of each compound. In the case of alcohols and acetates, the influence of the relative stereochemistry (cis vs trans) of isopropyl(ene) and the binding function was discussed. Copyright

Reactions of epoxides prepared from some monoterpenes with acetic anhydride on aluminosilicate catalysts

Reactions of epoxides prepared from α-, β-pinenes and camphene with acetic anhydride on aluminosilicate catalysts (clay K-10, zeolite β) were investigated affording various products of skeleton rearrangements: mono- and diacetates with five- and six-membered rings, and also with norbornane and pinane cores.

Reaction of cyclic allylic acetates with aliphatic alcohols in the presence of cerium(III) chloride

The reactions of selected allylic acetates with methanol, ethanol, n-propyl alcohol, isopropyl alcohol and tert-butyl alcohol in the presence of catalytic amounts of cerium(III) chloride are described. Allylic alkyl ethers, bis-allylic ethers and 1,3-dienes were obtained depending on the structure of the acetates.

Microbial Allyl Rearrangement and Resolution of Acetates of Unsaturated Cyclic Terpene Alcohols by Pseudomonas sp. NOF-5 Strain

Microbial hydrolysis of the acetates of unsaturated cyclic terpene alcohols by Pseudomonas sp.NOF-5 isolated from soil was investigated. (+/-)-trans-Carveyl acetate ((+/-)-trans-3) was enantioselectively hydrolyzed with NOF-5 strain to give (-)-trans-carveol ((-)-trans-2 of 86.6percent optical purity).However, the hydrolysis of (+/-)-cis-3 was less enantioselective, while (+/-)-piperitylacetate ((+/-)-6, a cis and trans mixture) was hydrolyzed to give the (-)-trans- and (-)-cis-piperitols ((-)-trans-5 and (-)-cis-5) in a poor optical yield.In this case, other tert-alcohols, (+)-trans- and (-)-cis-2-p-menthen-1-ols ((+/-)-trans-7 and (-)-cis-7, were also produced.Furthermore, microbial and enzymic allyl rearrangements of (+)-trans-6 and (-)-trans-verbenylacetate ((-)-trans-11) were studied.Biological treatment of (+)-trans-6 and (-)-trans-11 with NOF-5 or its esterase gave (+)-trans- and (-)-cis-7 and (+)-cis-3-pinen-2-ol ((+)-cis-12), respectively.

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.

NUCLEOPHILIC SUBSTITUTION OF ALKYL HALIDES BY ZINC SALTS-3 PREPARATION OF TERTARY ALKYL ESTERS AND ETHERS UNDER NON-SOLVOLYTIC CONDITIONS

Zinc salts of carboxylic acids, phenols and alcohols are found to react with tertiary alkyl halides in nonpolar solvents and in presence of a base yielding the corresponding esters and ethers in moderate to good yields.

Enzymic Resolution of (+/-)-Unsaturated Cyclic Terpene Alcohols via Asymmetric Hydrolysis of Corresponding Acetates by Microorganisms

Asymmetric hydrolysis of the acetates of (+/-)-cis and trans-carveols by microorganisms or their esterase produced chiral cis and trans-carveols and the acetates of their enantiomers.The enantioselectivity of the microbial hydrolysis and the optical purities of the products varied with the species of microorganisms.This method was also applied in separation of diastereomeric mixtures of (-)-carveols and (-)-7-epi-α-cyperols.