13487-27-9

Usage

Flammability and Explosibility

Nonflammable

Upstream product

• 1193-81-3 rac-1-cyclohexylethanol 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 108-22-5 Isopropenyl acetate 
• 932-66-1 1-cyclohexenyl methyl ketone 
• 931-50-0 cyclohexylmagnesium bromide 
• 64-19-7 acetic acid 
• 823-76-7 Cyclohexyl methyl ketone 
• 16526-90-2 cis-bicyclo<5.1.0>octane 

Downstream Products

• 695-12-5 vinylcyclohexane 
• 1003-64-1 ethylidenecyclohexane 
• 3113-99-3 (R)-1-cyclohexylethanol 
• 97011-89-7 (S)-(-)-1-cyclohexylethyl acetate 
• 58396-29-5 (R)-1-cyclohexylethyl acetate 

Relevant academic research and scientific papers

Sulfonic acid-functionalized periodic mesoporous organosilicas in esterification and selective acylation reactions

The application of sulfonic acid-functionalized periodic mesoporous organosilicas (PMOs) having either phenyl (1a) or ethyl (1b) bridging groups was investigated in the esterification of a variety of alcohols and fatty acids. It was found that 1b consistently exhibited higher catalytic performance than 1a in the described reaction. In particular, it was proposed that the superior catalytic activity of 1b in esterification of fatty acids with methanol is a result of adequate hydrophobic-hydrophilic surface balance in the ethyl PMO catalyst. In addition, the study of chemoselective acylation of 1,3-butanediol with dodecanoic acid with varied mesoporous silica-supported solid sulfonic acids including both 1a and 1b implies that there is a compromise between the reaction selectivity and the surface physicochemical properties of the employed catalyst. Our results clearly show that the catalyst having high surface hydrophilic nature gives high selectivity toward the formation of mono-acylated products whereas those with relatively high hydrophobic characteristics showed enhanced selectivity toward the formation of di-acylated products.

P-Toluenesulfonyl chloride as a new and effective catalyst for acetylation and formylation of hydroxyl compounds under mild conditions

The catalytic application of p-toluenesulfonyl chloride for efficient acetylation of various types of alcohols and phenols with acetic anhydride in solvent-free conditions is reported. Also structurally diverse alcohols were formylated using formic acid based on the use of catalytic amount of p-toluenesulfonyl chloride under solvent-free condition. The reactions were carried out in short reaction time and in good to excellent yields at room temperature.

N,N'-Diiodo-N,N'-1,2-ethanediylbis(p-toluenesulfonamide) as an efficient catalyst for acetylation of alcohols, phenols, amines, and thiols under solvent-free conditions

N,N'-Diiodo-N,N'-1,2-ethanediylbis(p-toluenesulfonamide) (NIBTS) is a highly efficient catalyst for the acetylation of alcohols, phenols, amines, and thiols under solvent-free conditions. Primary, secondary, tertiary alcohols; phenols; amines; and thiols can be easily acetylated in good to excellent yields at 80 C. Copyright Taylor & Francis Group, LLC.

Lentinus strigellus: a new versatile stereoselective biocatalyst for the bioreduction of prochiral ketones

Growing cells of the basiodiomycete Lentinus strigellus in potato-dextrose broth have been used for the first time as a biocatalyst in the stereoselective reduction of aromatic and aliphatic ketones. Most of the aromatic ketones were converted into the corresponding optically active alcohols in up to >99% enantiomeric excess under very mild reaction conditions. Among the aliphatic ketones tested, 2-octanone was enzymatically reduced by this microorganism to enantiopure (S)-2-octanol with almost complete conversion.

Enantiomer selective acylation of racemic alcohols by lipases in continuous-flow bioreactors

Continuous-flow mode enantiomer selective acetylations of racemic 1-phenylethanol, 1-cyclohexylethanol, and 1-phenylpropan-2-ol (rac-1a-c, respectively) with vinyl acetate were performed in small stainless steel packed-bed reactors filled with different commercial lipase preparations. In several lipase-filled columns, highly enantiomer selective (E > 100) kinetic resolutions of these alcohols were achieved. In most cases, comparison of the continuous-flow and batch mode (shake flask) biotransformations indicated similar enantiomer selectivities (E) but higher productivities (specific reaction rate: r) in the corresponding continuous-flow reaction. The effect of temperature (0-60 °C) and pressure (1-120 bar) on the continuous-flow acetylation of racemic 1-phenylpropan-2-ol was investigated in an immobilized Candida antarctica lipase B (CaLB) filled reactor. Pressure had no significant effect on r and E. Expectedly, a monotonous increase of specific reaction rate (r) was observed within this temperature range. Most surprisingly, the enantiomer selectivity had a maximum (E ～ 25, at 20 °C) and a minimum (E ～ 7, at 50 °C). The continuous-flow reactions in CaLB-filled columns were successfully applied for preparative scale kinetic resolutions of rac-1a-c.

Alternate-site enzyme promiscuity

(Chemical Equation Presented) Promiscuous reactions get around: It is shown that promiscuous enzyme-catalyzed reactions (i.e., the catalysis of distinctly different chemical transformations) can also take place at sites other than where the natural reaction occurs.

Lipase/aluminum-catalyzed dynamic kinetic resolution of secondary alcohols

(Chemical Equation Presented) Racemization wanted: The dynamic kinetic resolution of secondary alcohols can be achieved by a simple and readily available catalyst system. Substrate racemization is effected at room temperature by a combination of (racemic) 1,1′-bi-2-naphthol (binol) or 2,2′-biphenol with AIMe3, and a lipase performs enantiospecific acylation (see scheme).

Aminocyclopentadienyl ruthenium chloride: Catalytic racemization and dynamic kinetic resolution of alcohols at ambient temperature

Ruthenium-enzyme tandem catalysis: The novel racemization catalyst 1 improves the dynamic kinetic resolution (DKR) of secondary alcohols dramatically. The DKR proceeds at room temperature with isopropenyl acetate as an acyl donor. In addition, the DKR is faster even with much less lipase than in previous DKRs.

Lewis acid catalyzed acylation reactions: Scope and limitations

Acylation of alcohols, thiols, and sugars were studied with a variety of Lewis acids, and it was found that Cu- and Sn(OTf)2 are very efficient in catalyzing the reaction under mild conditions. Among these two catalysts, Cu(OTf)2 was preferred because of its lower cost and relatively higher yield of the acylated product. The reaction was studied in several solvents, but CH2Cl2 was preferred. It was also observed that the present method is suitable for acylation of tertiary alcohols. Sugars were also acylated without any epimerization at the anomeric center. It is further shown here that this method is also suitable for selective acylation of primary or secondary alcohols over tertiary ones.

One-step conversion of silyl/THP ethers into the corresponding acetates

A variety of silyl and THP ethers were directly converted into the corresponding acetates using acetic anhydride in the presence of a catalytic amount of Cu(OTf)2 in CH2Cl2. It was observed that MEM ethers could also be cl