93-92-5

Usage

Uses

Used in Fragrance Industry:
Styralyl acetate is used as a freshening compound in the fragrance industry, particularly in combination with Alkoxylated Phenols. Its unique scent profile adds a refreshing and green note to perfumes, colognes, and other scented products, enhancing their overall appeal and longevity.

Preparation

By acetylation of methyl phenyl carbinol; from benzaldehyde by reacting with magnesium methyl bromide and subse quent acetylation; from 1-bromoethylbenzene and silver acetate in acetic acid.

Synthesis Reference(s)

Journal of the American Chemical Society, 88, p. 1833, 1966 DOI: 10.1021/ja00960a057Synthetic Communications, 8, p. 33, 1978 DOI: 10.1080/00397917808062180

Flammability and Explosibility

Nonflammable

Metabolism

Although no published data exist on the metabolism of methylphenylcarbinyl acetate, it is likely that hydrolysis to the carbinol and acetic acid is the initial step. Williams (1959) reports studies in which 50% of a dose of (±)-methylphenylcarbinol given to rabbits was excreted as the glucuronide in the urine within 24 hr. There was some evidence of oxidation and demethylation, as mandelic and hippuric acids were found in the urine. Previously, El Masry, Smith

InChI:InChI=1/C10H12O2/c1-8(12-9(2)11)10-6-4-3-5-7-10/h3-8H,1-2H3/t8-/m1/s1

Upstream product

• 93-59-4 Perbenzoic acid 
• 769-59-5 3-phenyl-butan-2-one 
• 100-41-4 ethylbenzene 
• 98-85-1 1-Phenylethanol 
• 108-24-7 acetic anhydride 
• 127-09-3 sodium acetate 
• 622-24-2 2-phenylethyl chloride 
• 64-19-7 acetic acid 
• 75-16-1 methylmagnesium bromide 
• 100-52-7 benzaldehyde 
• 100-42-5 styrene 
• 546-67-8 lead(IV) tetraacetate 
• 13358-49-1 (R)-(1-phenyl)-1-ethyl benzoate 
• 672-65-1 (1-chloroethyl)benzene 

Downstream Products

• 100-42-5 styrene 
• 64-19-7 acetic acid 
• 40552-84-9 1-phenylethyl acetoacetate 
• 98-85-1 1-Phenylethanol 
• 4013-34-7 3-phenyl-2-oxabutane 
• 51256-30-5 2-(2,4-dinitrophenylthio)-1-phenyl-1-acetoxyethane 
• 1445-91-6 (S)-1-phenylethanol 
• 1517-69-7 (R)-1-phenylethanol 
• 16197-93-6 (S)-1-phenylethyl acetate 
• 16197-92-5 (R)-1-phenethyl acetate 
• 93-92-5 1-(-)-α-methylbenzyl acetate 
• 120-45-6 1-phenylethyl propanoate 
• 6531-13-1 1-[4-nitrophenyl]-1-ethanol 
• 80379-10-8 1-(2-nitrophenyl)ethan-1-ol 

Relevant academic research and scientific papers

Noncross-linked polystyrene nanoencapsulation of ferric chloride: A novel and reusable heterogeneous macromolecular Lewis acid catalyst toward selective acetylation of alcohols, phenols, amines, and thiols

Ferric chloride has been successfully nanoencapsulated for the first time on a non-cross-linked polystyrene matrix as the shell material via the coacervation technique. The resulting polystyrene nanoencapsulated ferric chloride was used as a novel and rec

Chiral phosphine-phosphoramidite ester ligand as well as preparation method and application thereof

The invention provides a method for preparing a phosphine-phosphoramidite ester ligand from a chiral beta-aminophosphine intermediate and an application of the phosphine-phosphoramidite ester ligand in an asymmetric reaction. Chiral N-(2-(phosphoryl)-1-phenethyl) amide is prepared from the chiral beta-aminophosphine intermediate through an asymmetric hydrogenation reaction of (Z)-(alpha-aryl-beta-phosphoryl) alkenyl amide, and then hydrolysis reduction. The preparation method comprises the following steps: dissolving newly-prepared chlorinated phosphite in toluene, adding a solution formed by dissolving the chiral phosphine-amine compound and triethylamine in toluene into an ice-water bath according to a molar ratio of the chiral phosphine-amine compound to the chlorinated phosphite to the triethylamine of 1: (1-2): (3-5), heating the reaction solution to 18-25 DEG C, stirring and reacting for 10-30 hours, filtering, and carrying out column chromatography to remove the solvent, and recrystallizing to obtain the required phosphine-phosphoramidite ligand. According to the present invention, the asymmetric hydrogenation reaction of the catalyst formed by the ligand and the metal precursor on the double bonds such as C = C, C = N, C = O and the like can achieve the enantioselectivity of 99%; the catalyst is high in activity, and TON reaches up to 10000.

Method for synthesizing styrallyl acetate from acetophenone

The invention provides a method for synthesizing styrallyl acetate from acetophenone, which comprises the following steps: reacting acetophenone with ketene under the catalysis of organic acid to obtain styrene acetate, and hydrogenating styrene acetate to obtain styrallyl acetate. The method is novel in synthetic route, the raw materials acetophenone and ketene are cheap and easy to obtain, the synthetic route is short, the yield is high, no equivalent acetic acid byproduct is produced, and the method has an obvious cost advantage.

Insight into the Mechanism of the Acylation of Alcohols with Acid Anhydrides Catalyzed by Phosphoric Acid Derivatives

Insight into the mechanism of a safe, simple, and inexpensive phosphoric acid (H3PO4)-catalyzed acylation of alcohols with acid anhydrides is described. The corresponding in situ-generated diacylated mixed anhydrides, unlike traditionally proposed monoacylated mixed anhydrides, are proposed as the active species. In particular, the diacylated mixed anhydrides act as efficient catalytic acyl transfer reagents rather than as Br?nsted acid catalysts simply activating acid anhydrides. Remarkably, highly efficient phosphoric acid (1-3 mol %)-catalyzed acylation of alcohols with acid anhydrides was achieved and a 23 g scale synthesis of an ester was demonstrated. Also, phosphoric acid catalyst was effective for synthetically useful esterification from carboxylic acids, alcohols, and acid anhydride. Moreover, with regard to recent developments in chiral 1,1′-bi-2-naphthol (BINOL)-derived phosphoric acid diester catalysts toward asymmetric kinetic resolution of alcohols by acylation, some phosphate diesters were examined. As a result, a 31P NMR study and a kinetics study strongly supported not only the acid-base cooperative mechanism as previously proposed by other researchers but also the mixed anhydride mechanism as presently proposed by us.

Trimethylsilyl Esters as Novel Dual-Purpose Protecting Reagents

Trimethylsilyl esters, AcOTMS, BzOTMS, TCAOTMS, etc., are inexpensive and chemically stable reagents that pose a negligible environmental hazard. Such compounds prove to serve as efficient dualpurpose reagents to respectively achieve acylation and trimethylsilylation of alcohols under acidic or basic conditions. Herein, a detailed study on protection of various substrates and new methodological investigations is described.

Sustainable electrochemical decarboxylative acetoxylation of aminoacids in batch and continuous flow

Introduction of acetoxy groups to organic molecules is important for the preparation of many active ingredients and synthetic intermediates. A commonly used and attractive strategy is the oxidative decarboxylation of aliphatic carboxylic acids, which entails the generation of a new C(sp3)-O bond. This reaction has been traditionally carried out using excess amounts of harmful lead(iv) acetate. A sustainable alternative to stoichiometric oxidants is the Hofer-Moest reaction, which relies on the 2-electron anodic oxidation of the carboxylic acid. However, examples showing electrochemical acetoxylation of amino acids are scarce. Herein we present a general and scalable procedure for the anodic decarboxylative acetoxylation of amino acids in batch and continuous flow mode. The procedure has been applied to the derivatization of several natural and synthetic amino acids, including key intermediates for the synthesis of active pharmaceutical ingredients. Good to excellent yields were obtained in all cases. Transfer of the process from batch to a continuous flow cell signficantly increased the reaction throughput and space-time yield, with excellent product yields obtained even in a single-pass. The sustainability of the electrochemical protocol has been examined by evaluating its green metrics. Comparison with the conventional method demonstrates that an electrochemical approach has a significant positive effect on the greenness of the process.

Ruthenium complex based on [N,N,O] tridentate -2-ferrocenyl-2-thiazoline ligand for catalytic transfer hydrogenation

A method for the synthesis of a new phosphine-free [N,N,O]-tridentate Schiff base ligand L1 using the 2-Ferrocenyl-2-thiazoline as scaffold was developed. The 1,2-disubstituted ferrocene-based ligand was assembled using as key strategy the directed ortho-metalation (DoM) in 2-ferrocenyl-2-thiazoline. L1 was successfully obtained in 83% of overall yield after two-step synthesis. The coordination ability of L1 towards Ru(II) was evidenced and the resulting complex was characterized by IR, UV-vis and EPR. Its catalytic performance was tested in transfer hydrogenation of a variety of substrates giving moderate to excellent conversions.

Environmentally responsible, safe, and chemoselective catalytic hydrogenation of olefins: ppm level Pd catalysis in recyclable water at room temperature

Textbook catalytic hydrogenations are typically presented as reactions done in organic solvents and oftentimes under varying pressures of hydrogen using specialized equipment. Catalysts new and old are all used under similar conditions that no longer reflect the times. By definition, such reactions are both environmentally irresponsible and dangerous, especially at industrial scales. We now report on a general method for chemoselective and safe hydrogenation of olefins in water using ppm loadings of palladium from commercially available, inexpensive, and recyclable Pd/C, together with hydrogen gas utilized at 1 atmosphere. A variety of alkenes is amenable to reduction, including terminal, highly substituted internal, and variously conjugated arrays. In most cases, only 500 ppm of heterogeneous Pd/C is sufficient, enabled by micellar catalysis used in recyclable water at room temperature. Comparison with several newly introduced catalysts featuring base metals illustrates the superiority of chemistry in water.

Activity and specificity studies of the new thermostable esterase EstDZ2

In this paper, we study the activity and specificity of EstDZ2, a new thermostable carboxyl esterase of unknown function, which was isolated from a metagenome library from a Russian hot spring. The biocatalytic reaction employing EstDZ2 proved to be an efficient method for the hydrolysis of aryl p-, o- or m-substituted esters of butyric acid and esters of secondary alcohols. Docking studies revealed structural features of the enzyme that led to activity differences among the different substrates.

KMnO4-catalyzed chemoselective deprotection of acetate and controllable deacetylation-oxidation in one pot

A novel and efficient protocol for chemoselective deacetylation under ambient conditions was developed using catalytic KMnO4. The stoichiometric use of KMnO4 highlighted the dual role of a heterogeneous oxidant enabling direct access to aromatic aldehydes in one-pot sequential deacetylation-oxidation. The reaction employed an alternative solvent system and allowed the clean transformation of benzyl acetate to sensitive aldehyde in a single step while preventing over-oxidation to acids. Use of inexpensive and readily accessible KMnO4 as an environmentally benign reagent and the ease of the reaction operation were particularly attractive, and enabled the controlled oxidation and facile cleavage of acetate in a preceding step. This journal is