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. Pd-catalyzed reaction of benzyl acetates with active methylene compounds. The reaction was initiated by transferring by syringe a solution of potassium tert-butoxide (2.5 mmol) in THF (10 ml) to the vessel. We use cookies to help provide and enhance our service and tailor content and ads. Two hydroxyl groups of the obtained compound were acetylated by heating at 100oC with sodium acetate and acetic anhydride in acetic acid to produce the requested 2-acetoxy-5-acetylbenzyl acetate (23.1.19). 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. 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. For example, allyl β-ketocarboxylates are converted to trialkyltin β-ketocarboxylates. In most cases of different combinations of dienophiles and dienes, the reaction rate at near-critical hydrothermal conditions is faster than at low-temperature reaction conditions [2]. XPS can distinguish between those undesired behaviors. Palladium-catalyzed cross-coupling between benzylic electrophiles and aryl organometallics, Palladium-catalyzed cross-coupling of alkenyl stannanes with benzylic bromides give the di- or trisubstituted olefins with complete retention of the double bond configuration (Scheme 34).100,101. 2-Phenylethanol and benzyl alcohol react to considerable proportions to the corresponding ethers [63,108]. Reprinted with permission from Gatla, S., Mathon, O., Rogalev, A., et al. 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. It is collected and used by the bees as an intra-specific pheromone; In apiculture benzyl acetate is used as a bait to collect bees. Complex polypeptide synthesis often requires the use of several protection–deprotection strategies. Volatile compounds identified from bee venom. Oxide supported Pd-containing materials are often used. Pd-catalyzed cross-coupling of benzyl acetates with dimethylmalonates. Ni-catalyzed reactions of phenyl acetonitrile derivatives with benzyl pivalates. 2-Heptanone is another volatile component and the principal aggression-provoking factor among sting pheromones [166]. This high demand underlines the importance of an environmentally benign alternative to the established process. In contrast to XPS, this technique is bulk-sensitive. The product was hydrolyzed to (hydroxymethyl)phenol (23.1.22) using hydrochloric acid at room temperature. Final debenzylation via hydrogenation on Pd/C catalyst produced the desired albuterol (23.1.4) [32-37] (Scheme 23.1.). Unfortunately, such deactivation is observed often and hinders the application of a promising system in many cases. Found in many essential oils including geranium, citronella, lavender, petitgrain and sweet marjoram. 4). 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. Such investigations are very sensitive for changes of Pd 4d valence band. The solvent was removed and the phosphonate mixture was filtered from the salts. Isopentyl acetate and (Z)-11-eicosen-l-ol are known to be pheromones that warn bees of danger, thus stimulating the stinging reaction. Scheme 54. The interested reader is referred to the reviews on organic reactions in high-temperature liquid and supercritical water [2,22,23,25,27]. The Journal of Physical Chemistry C 121, 3854-3861. Alloxycarbonyl–NH deprotection is rapid; allyl amine formation is not competitive. Contamination by tin residues is apparently not a problem. The second substitution occurs at a rate lower than the first. Reaction characteristics of Diels–Alder reactions in high-temperature liquid water and supercritical water are attributed to the unique properties of near-critical and supercritical water [27,119,120]. Under these conditions, 94% of the benzyl acetate was consumed to yield benzyl methyl methylphosphonate and dibenzyl methylphosphonate (94:6 ratio). After 45 s, the reaction was quenched with saturated brine (2 ml). Hydrothermal and Supercritical Water Processes, Supercritical Fluid Science and Technology, . The limited surface sensitivity of XPS does not allow such clear distinction. (Benzyl acetate is not a terpene derivative but is found in many essential oils.). Benzyl acetate is an organic ester with the molecular formula C9H10O2. Natural sources of benzyl acetate include varieties of flowers like jasmine (Jasminum), and fruits like pear, apple, etc. Therefore, selectivity can be influenced by increased pressure and the ratio of the endocomponent to the exocomponent enhanced [2,117,118]. No tin is left on the deprotected peptide, and the tin by-products are sufficiently soluble in the reaction solvent (DMF, CH2Cl2). It is a constituent of jasmin and of the essential oils of ylang-ylang and neroli. A temperature of 600°C was found to be optimal. Scheme 55. Scheme 36. Sintering leads to a decrease of the fraction of the active species which is detected by XPS due to the lower amount of surface atoms if the particles grow. Table 12. Fruity, floral, light rose-like odour. The difference between the two protocols was attributed to base-induced elimination of HCN occurring for the stilbene formation, favoring trans-configured olefins predominantly. In alkali, 4-(acetoxymethyl)imidazole (160) is hydrolyzed ∼ 105 times as fast as benzyl acetate, CH3COOCH2Ph. Palladium-catalyzed cross-coupling between secondary benzylic bromides and Grignard reagents. Copyright 2017 American Chemical Society. Similarly, the palladium-catalyzed reaction of aryl- or vinyl Grignard reagents with secondary benzylic bromides gives the coupling products in good yields (Scheme 36).103 The reaction proceeds with inversion of configuration. It must be noted that XPS is an important piece of a puzzle for the establishment of reliable structure–property relationships, but XPS must be embedded in comprehensive analytical studies using other methods, for example, X-ray diffraction, electron microscopy, temperature programmed investigation (TPO, TPD) and, if possible, X-ray absorption spectroscopy (XAS or XAFS) to obtain deeper understanding of the catalysts. Further as a flavoring agent it is also used to impart jasmine or apple flavors to various cosmetics and personal care products like lotions, hair creams etc..[1], It is one of many compounds that is attractive to males of various species of orchid bees. [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. On le trouve à l'état naturel dans beaucoup de fleurs. Benzyl acetate is an organic ester with the molecular formula C9H10O2. These findings revealed clearly that an active catalyst must have both species of Pd. [2], Industrially benzyl acetate is used as a medium of extraction in extraction of plastics, resin, cellulose acetate, cellulose nitrate, oils and lacquers. 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. It seemed that the incorporated Sb favors the formation of the undesired carbon deposits. Unfortunately, however, significant amounts of styrenes were observed, probably due to competitive β-hydride elimination with secondary benzyl acetates. (2017). L'acétate de benzyle C9H10O2 ou CH3-CO-O-CH2-C6H5 Benzylic halides (entries 1 and 5–9) as well as benzyl acetates, carbonates, phosphates, or tosylates (entries 2–4 and 6) can be coupled. The latter was proposed to rapidly react with CO to afford an acyl cobalt intermediate that promotes a hydrosilylation. Ruben Vardanyan, Victor Hruby, in Synthesis of Best-Seller Drugs, 2016. The odour and uses of Benzyl Acetate Odour=> sweet floral fruity fresh sweet aromatic floral fruity jasmin ylang Powerful but a thin~~ sweet floral fresh and light fruity odor reminiscent of Jasmin Gardenia Muguet Lily and other flowers Very extensively used in perfumery from the lowest priced industrialodors to the most highly appreciated cosmetic fragrances often constituting the main ingredient in a …