42288-75-5

Usage

Uses

Used in Fragrance Industry:
Cyclohexyl-phenylacetate is used as a fragrance ingredient for its floral odor, enhancing the scent profiles of cosmetics, personal care products, and perfumes. Its ability to contribute a distinct and appealing aroma makes it a valuable component in the creation of various scented products.
Used in Flavorings:
Beyond its aromatic applications, cyclohexyl-phenylacetate is also utilized in flavorings to impart a specific taste or aroma to food products, beverages, and other consumables, thereby enriching the sensory experience of these items.
Used as a General Solvent:
Cyclohexyl-phenylacetate serves as a general solvent in various chemical processes, facilitating the dissolution of other substances and enabling reactions to occur more efficiently. Its solvent properties make it a versatile component in a range of industrial applications.
Used in Chemical Intermediates:
In the production of other organic compounds, cyclohexyl-phenylacetate may be employed as a chemical intermediate. Its reactivity and structural features allow it to participate in the synthesis of a variety of chemical products, contributing to the broader chemical industry's output.
While the provided materials do not specify any limitations or restrictions on the use of cyclohexyl-phenylacetate, it is important to note that, as with any chemical compound, its use should be managed with consideration for safety, environmental impact, and regulatory compliance.

InChI:InChI=1/C14H18O2/c15-14(11-12-7-3-1-4-8-12)16-13-9-5-2-6-10-13/h1,3-4,7-8,13H,2,5-6,9-11H2

Upstream product

• 68484-72-0 cyclohexyl 2-phenylacetimidate hydrochloride 
• 103-82-2 phenylacetic acid 
• 108-93-0 cyclohexanol 
• 108-85-0 1-bromocyclohexane 
• 536-74-3 phenylacetylene 
• 110-83-8 cyclohexene 
• 101-41-7 benzeneacetic acid methyl ester 
• 140-29-4 phenylacetonitrile 
• 109853-53-4 3-(2-phenylacetyl)-1,3-oxazolidin-2-one 
• 103-83-3 N,N'-dimethylbenzylamine 
• 260783-80-0 N,N,N--trimethyl--1--phenylmethanaminium trifluoromethanesulfonate 
• 201230-82-2 carbon monoxide 
• 28170-07-2 benzyl phenyl carbonate 
• 100-51-6 benzyl alcohol 

Downstream Products

• 110-83-8 cyclohexene 
• 100-41-4 ethylbenzene 
• 60-12-8 2-phenylethanol 
• 880348-51-6 2-phenyl-acrylic Acid Cyclohexyl Ester 
• 80858-47-5 (2-(cyclohexyloxy)ethyl)benzene 

Relevant academic research and scientific papers

A solvent-reagent selection guide for Steglich-type esterification of carboxylic acids

The Steglich esterification is a widely employed method for the formation of esters under mild conditions. A number of issues regarding the sustainability of this transformation have been identified, chiefly the use of hazardous carbodiimide coupling reagents in conjunction with solvents with considerable issues such as dichloromethane (DCM) and N,N-dimethylformamide (DMF). To overcome these issues, we have developed a solvent-reagent selection guide for the formation of esters via Steglich-type reactions with the aim of providing safer, more sustainable conditions. Optimum reaction conditions have been identified after high-throughput screening of solvent-reagent combinations, namely the use of Mukaiyama's reagent (Muk) in conjunction with solvent dimethyl carbonate (DMC). The new reaction conditions were also exemplified through the synthesis of a small selection of building-block like molecules and includes the formation of t-butyl esters.

Benzyne-Mediated Esterification Reaction

A benzyne-mediated esterification of carboxylic acids and alcohols under mild conditions has been realized, which is made possible via a selective nucleophilic addition of carboxylic acid to benzyne in the presence of alcohol. After a subsequent transesterification with alcohol, the corresponding esters can be produced efficiently. This benzyne-mediated protocol can be used on the modification of Ibuprofen, cholesterol, estradiol, and synthesis of nandrolone phenylpropionate. In addition, benzyne can also be used to promote lactonization and amidation reaction.

Preparation of Organic Nitrates from Aryldiazoacetates and Fe(NO3)3·9H2O

A thermal protocol is reported for the formal insertion of nitric acid into aryldiazoacetates using Fe(NO3)3·9H2O. This strategy is mild and high yielding and allows the preparation of a large variety of members of an unprecedented family of organic nitrates. The nitrate group can be also readily transformed into other functional groups and heterocyclic moieties and can possibly allow new biological explorations of untapped potential associated with their NO-releasing ability.

Palladium-Catalyzed Decarboxylative Carbonylative Transformation of Benzyl Aryl Carbonates: Direct Synthesis of Aryl 2-Arylacetates

A procedure on palladium-catalyzed decarboxylative alkoxycarbonylation of carbonates for the synthesis of aryl 2-arylacetates has been developed. A broad range of aryl 2-arylacetates were obtained in good yields under mild conditions under a carbon monoxide atmosphere. Interestingly, other alcohols can be added as nucleophiles as well, and the corresponding esters were also obtained in good yields.

Palladium-catalyzed carbonylation of benzylic ammonium salts to amides and esters: Via C-N bond activation

An efficient palladium-catalyzed carbonylation reaction of readily available quaternary ammonium salts with CO is reported for the first time to afford arylacetamides and arylacetic acid esters via benzylic C-N bond cleavage. This protocol features mild reaction conditions under atmospheric pressure of CO, a redox-neutral process without an additional oxidant, and a broad substrate scope for various kinds of amines, alcohols and phenols.

Ni-Catalyzed chemoselective alcoholysis of: N -acyloxazolidinones

Although N-acyloxazolidinone-based (catalytic) asymmetric synthetic methodologies occupy an important position in modern organic synthesis, the catalytic cleavage of a chiral auxiliary remains underdeveloped. We report the Ni(cod)2/bipyr.-catalyzed alcoholysis of N-acyloxazolidinones to deliver esters. The reaction is broad in scope for both N-acyloxazolidinone substrates and alcohol nucleophiles, and displays good functional group tolerance and excellent chemoselectivity. A gram-scale methanolysis allowed the enantioselective synthesis of the C22-C26 segment of a close analogue of the potent immunosuppressant agent FK506.

2,2,6,6-Tetramethylpiperidinium triflate (TMPT): a highly selective and self-separated catalyst for esterification

An eco-friendly and readily accessible 2,2,6,6-tetramethylpiperidinium triflate was found as highly-selective and self-separated catalyst for esterification under solvent-free condition. The X-ray crystallography revealed that it formed a ‘hydrophobic wall’ which could effectively eliminate the generated water from the reactive sites. Moreover, it could precipitate from the reaction system with excellent recovery ratio (>99%) and be reused for ten times without any significant loss of activity.

SO3H and NH2+ functional carbon-based solid acid catalyzed transesterification and biodiesel production

A SO3H and NH2+ functional carbon-based solid acid was used as a highly active heterogeneous catalyst for the transesterification of various carboxylic methyl esters with alcohols under mild conditions. It also showed high catalytic performance for transesterification of triolein with methanol or isopropanol. Furthermore, it was able to catalyze simultaneous esterification and transesterification of rice oil and butter respectively, the yields of biodiesel obtained were up to 94%, and the catalyst could be easily recovered and reused more than ten times without loss of activity, which indicated the carbon-based solid acid was a potential catalyst for the biodiesel industry.

The carbon material functionalized with NH2+ and SO3H groups catalyzed esterification with high activity and selectivity

A novel carbon-based solid acid was conveniently prepared by heating a mixture of d-glucose, p-toluenesulfonic acid and diphenylammonium tosylate. Its structure was measured by XRD, FT-IR, XPS, 13C MAS NMR and EA to illustrate that the carbon material has been functionalized with NH2+ and SO3H groups and has a strong "hydrophobic effect". It can be used to catalyze the esterification reaction of carboxylic acids with equimolar amounts of sterically demanding and acid-sensitive alcohols with high reactivity (yield up to 90%) and selectivity (up to 95%) in heptane at 80 °C. It could be easily recovered and reused more than ten times without loss of activity.

A lewis acid-promoted pinner reaction

Carbonitriles and alcohols react in a Lewis acid-promoted Pinner reaction to carboxylic esters. Best results are obtained with two equivalents of trimethylsilyl triflate as Lewis acid. Good yields are achieved with primary alcohols and aliphatic or benzylic carbonitriles, but the straightforward synthesis of acrylates and benzoates starting with acrylonitrile and benzonitrile, respectively, is similarly possible. Phenols are not acylated under these reaction conditions. The method has been used for the first total synthesis of the natural product monaspilosin. In the reaction of benzyl alcohols variable amounts of amides are formed in a Ritter-type side reaction.