benzyl acetate uses

A temperature of 600°C was found to be optimal. The latter was found for the Pd, Sb catalyst used in the acetoxylation of toluene: the carbon amount at the surface increased dramatically with the deactivation. Usually, sintering of nanoparticles or deposition of undesired by-products like carbon species on the surface of the active particles are discussed as reasons for this undesired behavior. Prompted by Murai's report, Legros and Fiaud studied the possibility of promoting Pd-catalyzed C–C bond-forming reactions of benzyl acetates with dimethylmalonates (Scheme 54).98 The authors found that the reaction remained limited to benzylic acetates derived from substrates with extended π-backbones, an observation that was attributed to the requirement for partial dearomatization via π-allyl-Pd complexes. Scheme 53. Christopher M. Timperley, in Best Synthetic Methods, 2015. The first proposed synthesis of albuterol (23.1.4) started from chloromethylation of 4-hydroxyacetophenone (23.1.17) in formaldehyde/hydrochloric acid solution on passing hydrogen chloride gas to produce 3-(chloromethyl)-4-hydroxyacetophenone (23.1.18) [31].

Whereas the acetoxylation of ethylene to vinyl acetate is a well-established process, another important acetate compound, benzyl acetate, is still manufactured by the harmful chlorination of toluene and subsequent conversion of benzyl chloride and alkali acetate. This high demand underlines the importance of an environmentally benign alternative to the established process. Scheme 34. It represents a first-line therapy because it offers rapid bronchodilation, usually relieving bronchospasm within minutes. [citation needed], InChI=1S/C9H10O2/c1-8(10)11-7-9-5-3-2-4-6-9/h2-6H,7H2,1H3, InChI=1/C9H10O2/c1-8(10)11-7-9-5-3-2-4-6-9/h2-6H,7H2,1H3, Except where otherwise noted, data are given for materials in their, https://en.wikipedia.org/w/index.php?title=Benzyl_acetate&oldid=983059195, Chemical articles with multiple compound IDs, Multiple chemicals in an infobox that need indexing, Pages using collapsible list with both background and text-align in titlestyle, Articles containing unverified chemical infoboxes, Articles with unsourced statements from September 2008, Creative Commons Attribution-ShareAlike License, This page was last edited on 12 October 2020, at 00:43. Hydrolysis of benzaldehyde diethyl acetal in aqueous KOH solution is followed by a Cannizarro disproportionation, where benzyl alcohol and benzoic acid are predominantly formed [27,48] at T = 254 °C and an acetal to KOH molar ratio of 4. The same effect can be observed here because some species deposit on the active species, but, additionally, a clear increase of the components of the deposit should be detected with XPS. Alloxycarbonyl is easily introduced using inexpensive and commercially available allyl chloroformate. While benzyl acetate is mainly used in flavor and fragrance industry, benzyl alcohol is widely used as solvent for inks, paints, coatings, and as intermediate in chemical industry. Subsequently, Kuwano disclosed an intramolecular protocol in which the malonate and the acetate motif were connected through a tether.100 Recently, Hirano and Miura reported the successful Pd/(R)-H8-BINAP-catalyzed asymmetric benzylic alkylation of π-extended benzyl pivalates with a wide range of active methylene compounds.101 Mal and Roy then described heterobimetallic Pd–Sn catalysts capable of promoting substitution reactions of benzylic alcohol substrates, although the reactivity resembles the classical Friedel–Crafts-type reaction.102. In 2010, Chruma described an otherwise similar transformation using benzyl diphenylglycinate imines; in this case, however, decarboxylation results in benzophenone imine protected amines as products.104. Alloxycarbonyl-protected amino acids are not susceptible to racemization during protection or deprotection. Floral, fruity, sweet and herbaceous odour. In the early 1990s, Murai and coworkers reported a cobalt-catalyzed carbonylation–hydrosilylation sequence using benzyl acetate substrates (Scheme 53).97 The reaction converted these compounds into the corresponding homobenzylic silyl ethers using carbon monoxide and trimethylsilane. Fruity, floral, light rose-like odour. Complex polypeptide synthesis often requires the use of several protection–deprotection strategies. No tin is left on the deprotected peptide, and the tin by-products are sufficiently soluble in the reaction solvent (DMF, CH2Cl2). Esters are formed or hydrolyzed quite readily in aqueous solution [23]. By continuing you agree to the use of cookies. It seemed that the incorporated Sb favors the formation of the undesired carbon deposits. DPEPhos=(Oxydi-2,1-phenylene)bis(diphenylphosphine). The last was directly brominated with bromine in chloroform at room temperature, providing 2-acetoxy-5-(2-bromo-acetyl), X-Ray Photoelectron Spectroscopy for Investigation of Heterogeneous Catalytic Process. Albuterol is generally well tolerated and any side effects observed, such as restlessness, irritability, or nervousness, are a predictable extension of its pharmacology [38-40]. In alkali, 4-(acetoxymethyl)imidazole (160) is hydrolyzed ∼ 105 times as fast as benzyl acetate, CH3COOCH2Ph. Similar to most other esters, it possesses a sweet and pleasant aroma, owing to which, it finds applications in personal hygiene and health care products. However, one disadvantage of XPS we already mentioned earlier is not being able to distinguish between the outermost layer and the near-surface region. J. Radnik, in Encyclopedia of Interfacial Chemistry, 2018. Scheme 54. It is formed by the condensation of benzyl alcohol and acetic acid.

Benzylic halides (entries 1 and 5–9) as well as benzyl acetates, carbonates, phosphates, or tosylates (entries 2–4 and 6) can be coupled. More interestingly, the authors described the use of chiral ligands in combination with racemic secondary benzyl acetates, obtaining promising yields and stereoinductions with (S,S)-BDPP or (R,R)-i-Pr-DUPHOS.

Benzyl methyl methylphosphonate BnO(MeO)P(O)Me (256). Model for the different stages of the catalyst as prepared, active, and deactivated. Benzyl acetate is an organic ester with the molecular formula C9H10O2. Due to this incorporation, an additional Pd state appeared with an excess electron charge, because electron density was transferred from Sb to Pd (Fig. La dernière modification de cette page a été faite le 6 décembre 2019 à 12:08. Floral and fruity odour (typical of jasmin). On le trouve à l'état naturel dans beaucoup de fleurs. δP (121.5 MHz, CDCl3) 32.5 ppm.

3). In all cases, products underwent net inversion of configuration. Benzyl alcohol is generated from the putative tin alkoxide intermediate by workup with aqueous acid. It is important that dienophile and dienes dissolve in the reaction solvent. Several methods exist for the cross-coupling of benzylic electrophiles with different organometallic reagents (Table 12).90–99 Organoborane reagents are employed most frequently (entries 1–5), but methods for the coupling of organosilane (entry 6), organotin (entry 7), organozinc (entry 8), or organoindium reagents (entry 9) have also been developed.

Such investigations are very sensitive for changes of Pd 4d valence band. Additional temperature programmed oxidation (TPO) experiments were helpful to identify the nature of the carbon species and to distinguish between carbon deposited on the surface and incorporated in the near surface, because of their peak maxima at different temperatures. Unfortunately, such deactivation is observed often and hinders the application of a promising system in many cases. The allyl and alloxycarbonyl strategy is orthogonal to the benzyloxycarbonyl (BOC) and the t-butoxycarbonyl strategies (t-BOC).17–18, When a proton source is omitted from the recipe, reductive cleavage results in isolable tin-containing products. Ni-catalyzed reactions of phenyl acetonitrile derivatives with benzyl pivalates. The authors proposed that the reaction proceeds through the initial formation of silyl–cobalt intermediates, which set the stage for an oxidative addition en route to trimethylsilyl acetate and a benzyl cobalt species. Isopentyl acetate and (Z)-11-eicosen-l-ol are known to be pheromones that warn bees of danger, thus stimulating the stinging reaction. Unfortunately, however, significant amounts of styrenes were observed, probably due to competitive β-hydride elimination with secondary benzyl acetates. Tunge and Chruma have reported decarboxylative processes via C(sp3)–O cleavage for the installation of alkynes and ketones at the benzylic position (Scheme 56).103 Unfortunately, the scope of these reactions is essentially limited to substrates with π-extended backbones. (Z)-11-Eicosen-l-ol has been identified by gas chromatography-mass spectrometry as a major volatile component (ca.

Co-catalyzed carbonylation/hydrosilylation of benzyl acetates. est l'ester de l'acide acétique et de l'alcool benzylique. Thus, an electron transfer from incorporated Sb to metallic Pd was clearly verified.

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