68366-66-5

Basic information

• Product Name: (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl cyclohexanecarboxylate
• Synonyms: (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl cyclohexanecarboxylate
• CAS NO: 68366-66-5
• Molecular Weight: 266.424
• Mol File: 68366-66-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl cyclohexanecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl cyclohexanecarboxylate(68366-66-5)
• EPA Substance Registry System: (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl cyclohexanecarboxylate(68366-66-5)

Safety Data

• Hazardous Substances Data: 68366-66-5(Hazardous Substances Data)

Upstream product

• 2216-51-5 (-)-menthol 
• 221887-36-1 2,2,2-tribromoethyl cyclohexanecarboxylate 
• 35665-26-0 N-benzylcyclohexanecarboxamide 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 1127-08-8 cyclohexanedicarboxylic acid 
• 98-89-5 Cyclohexanecarboxylic acid 

Downstream Products

• 258265-83-7 1-Cyclohexyl-2-((R)-toluene-4-sulfinyl)-ethanone 
• 68326-61-4 1-Cyclohexyl-2-((S)-toluene-4-sulfinyl)-ethanone 
• 98-89-5 Cyclohexanecarboxylic acid 

Relevant articles and documents

Nickel-Catalyzed Esterification of Aliphatic Amides

Recent studies have demonstrated that amides can be used in nickel-catalyzed reactions that lead to cleavage of the amide C?N bond, with formation of a C?C or C?heteroatom bond. However, the general scope of these methodologies has been restricted to amides where the carbonyl is directly attached to an arene or heteroarene. We now report the nickel-catalyzed esterification of amides derived from aliphatic carboxylic acids. The transformation requires only a slight excess of the alcohol nucleophile and is tolerant of heterocycles, substrates with epimerizable stereocenters, and sterically congested coupling partners. Moreover, a series of amide competition experiments establish selectivity principles that will aid future synthetic design. These studies overcome a critical limitation of current Ni-catalyzed amide couplings and are expected to further stimulate the use of amides as synthetic building blocks in C?N bond cleavage processes.

Widely useful DMAP-catalyzed esterification under auxiliary base- and solvent-free conditions

With regard to atom economy and E-factor, catalytic condensation of carboxylic acids with equimolar amounts of alcohols is the most desirable. Although several highly active dehydration catalysts have been reported, more efficient alternatives are still strongly needed because the dehydrative esterification of tertiary alcohols, phenols, acid-sensitive alcohols, amino acids, and hardly soluble alcohols has never proceeded satisfactorily. Here we report new insights into the classical DMAP-catalyzed acylation of alcohols: surprisingly, only a 0.05-2 mol % of DMAP can efficiently promote acylation of alcohols with acid anhydrides under auxiliary base- and solvent-free conditions to give the corresponding esters in high yields. Furthermore, we achieved the recovery and reuse of commercially available polystyrene-supported DMAP without using any solvents. These serendipitous findings provide widely useful and environmentally benign esterification methods, which might be more practical and reliable than catalytic dehydrative condensation methods, in particular, for the less reactive alcohols which hardly condense with carboxylic acid directly.

One-pot synthesis of amides and esters from 2,2,2-trihaloethyl esters using phosphorus(III) reagents

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