7774-44-9

Usage

Chemical Properties

Cyclohexyl isovalerate has an apple- and banana-like aroma.

Preparation

From cyclohexane and isovaleric acid in the presence of perchloric acid.

InChI:InChI=1/C11H20O2/c1-9(2)8-11(12)13-10-6-4-3-5-7-10/h9-10H,3-8H2,1-2H3

Upstream product

• 503-74-2 3-methylbutyric acid 
• 108-93-0 cyclohexanol 
• 1468-39-9 Isovaleric anhydride 
• 108-12-3 isopentanoyl chloride 
• 123-51-3 i-Amyl alcohol 
• 201230-82-2 carbon monoxide 
• 75-65-0 tert-butyl alcohol 
• 115-11-7 isobutene 

Relevant academic research and scientific papers

Synthesis of cyclohexyl isovalerate by carbonylation of isobutylene with carbon monoxide and cyclohexanol in the presence of Pd(PPh3)4?PPh3?TsOH and its antimicrobial activity

A procedure has been developed for the synthesis of cyclohexyl isovalerate by reaction of isobutylene with carbon monoxide and cyclohexanol in the presence of the three-component catalytic system Pd(PPh3)4?PPh3?TsOH. Cyclohexyl isovalerate showed a pronounced antibacterial activity.

Palladium-Catalyzed Carbonylation of sec- and tert-Alcohols

A general palladium-catalyzed synthesis of linear esters directly from sec- and tert-alcohols is described. Compared to the classic Koch–Haaf reaction, which leads to branched products, this new transformation gives the corresponding linear esters in high yields and selectivity. Key for this protocol is the use of an advanced palladium catalyst system with L2 (pytbpx) as the ligand. A variety of aliphatic and benzylic alcohols can be directly used and the catalyst efficiency for the benchmark reaction is outstanding (turnover number up to 89 000).

Ruthenium pincer-catalyzed cross-dehydrogenative coupling of primary alcohols with secondary alcohols under neutral conditions

Cross-dehydrogenative coupling of primary alcohols with secondary alcohols to obtain mixed esters with the liberation of molecular hydrogen is achieved in high yield and good selectivity under neutral conditions, using a bipyridyl-based PNN ruthenium(II) pincer catalyst. Copyright

Steric effects in the uncatalyzed and DMAP-catalyzed acylation of alcohols - Quantifying the window of opportunity in kinetic resolution experiments

The kinetics of the reaction of several alcohols (benzyl alcohol, ethanol, 1-phenylethanol, cyclohexanol, and 1-methyl-1-phenylethanol) with a selection of anhydrides (acetic anyhydride, propionic anhydride, isobutyric anhydride, isovaleric anhydride, and pivalic anhydride) as catalyzed by 4-(N,N-dimethylamino)pyridine (DMAP)/triethyl amine have been studied in CH 2Cl2 at 20°C. In all cases the reaction kinetics can be described by rate laws containing a DMAP-catalyzed term and an uncatalyzed (back-ground) term. The rate constants for the background reaction respond sensi tively to changes in the steric demand of the alcohol and the anhydride substrates, making the reaction of cyclohexanol with acetic anhydride 526 times faster than the reaction with pivalic anhydride. Steric effects are even larger for the catalyzed reaction and the reactivity difference between acetic and pivalic anhydride exceeds a factor of 8000 for the reaction of cyclohexa nol. There is, however, no linear correlation between the steric effects on the catalyzed and the uncatalyzed part. As a consequence there are substrate combinations with dominating catalytic terms (such as the reaction of benzyl alcohol with isobutyric anhydride), while other substrate combinations (such as the reaction of cyclohexanol with pivalic anhydride) are characterized through a dominating background process. The implications of these findings for the kinetic resolution of alcohols are discussed.