Butyl Phenylacetate

A flavor is tried at several different levels and in different mediums until the most characteristic one is selected. This is important because the character of a material is known to change quaUty with concentration and environment. For example, anethole, ben2aldehyde, and citral taste different with and without acid. Gamma-decalactone has different characters at different levels of use. -/ fZ-Butyl phenylacetate with acid is strawberry or fmity without acid it is creamy milk chocolate. 2,5-Dimethyl-4-hydroxy-3-(2Fi)-furanone with acid is strawberry without acid it is caramel or meat. 

The method described is successfully used for the alkylation and aralkylation of ethyl and /-butyl phenylacetate.3 The alkylation of ethyl phenylacetate with methyl iodide, M-butyl bromide, benzyl chloride, and a-phenylethyl chloride affords the corresponding pure monoalkylation products in 69%, 91%, 85%, and 70% (erythro isomer) yields, respectively. The alkylation of /-butyl phenylacetate with methyl iodide, M-butyl bromide, a-phenylethyl chloride, and /3-phenylethyl bromide gives the corresponding pure monoalkylated products in 83%, 86%, 72-73%, and 76% yields, respectively. 

Butylation of ethyl phenylacetate, /-butyl phenylacetate, and ethyl 2-phenylhexanoate has also been accomplished with M-butyl bromide and sodium hydride in refluxing monoglyme in 64%, 66%, and 56% yields, respectively.6 In contrast to the sodium amide reactions above, however, careful fractionation of the crude products was required to obtain pure products. 

With the same procedure /-butyl phenylacetate has been prepared in 47% yield.4 When esters of less common alcohols were prepared, anhydrous ether was used as a solvent instead of excess alcohol. Equivalent amounts of alcohol, n-butyllithium, and acid chloride were employed. Thus the triethylcarbinol ester of p-toluic acid and the 2,2-diphenylethanol ester of benzoic acid have been prepared in 72 and 70% yields, respectively. 

Benzaldehyde is formed in the liquid-phase oxidation of f-butyl phenylacetate via a hydroperoxide and also by a non-radical pathway, probably via a dioxetane intermediate both reactions are catalysed by benzoic acid. The kinetic parameters have been calculated by solving an inverse kinetic equation.258... 

This important fragrance material probably was introduced in commercial perfumery during the first decade of the twentieth century with the discovery of the Bouveault-Blanc reduction of esters by sodium and an alcohol (10). This is the first of several methods of preparation shown in Figure 16. Large quantities of phenylethyl alcohol were made by sodium reduction of butyl phenylacetate in normal butanol. The basic raw materials were readily available at low cost from benzyl chloride, sodium cyanide and fermentation butanol. 

Several new catalytic asymmetric protonations of metal enolates under basic conditions have been published to date. In those processes, reactive metal enolates such as lithium enolates are usually protonated by a catalytic amount of chiral proton source and a stoichiometric amount of achiral proton source. Vedejs et al. reported a catalytic enantioselective protonation of amide enolates [35]. For example, when lithium enolate 43, generated from racemic amide 42 and s-BuLi, was treated with 0.1 equivalents of chiral aniline 31 followed by slow addition of 2 equivalents of ferf-butyl phenylacetate, (K)-enriched amide 42 was obtained with 94% ee (Scheme 2). In this reaction, various achiral acids were... 

Anisyl Alcohol 653 Butyl Phenylacetate 668 Cuminic Aldehyde... 

PHENYLACETATE n-BUTYL PHENYLACETATE PHENYLETHANOIC ACID BUTYL ESTER... 

Acety Ipyri di ne 58 Butyl phenylacetate 106 3,4-Dimethyl-1,2-cyclopentanedione... 

Benzeneacetic acid, butyl ester butyl phenylacetate 603, 3370... 

Acetic acid, oleyl ester. See Oleyl acetate Acetic acid, oxo-. See Glyoxalic acid Acetic acid palladium salt Acetic acid palladium (2+) salt. See Palladium diacetate Acetic acid pentyl ester. See Amyl acetate Acetic acid, phenyl-, butyl ester. See Butyl phenylacetate... 

Butyl benzene acetate. See Butyl phenylacetate, 5-t-ButyM, 3-benzenedicarboxylic acid CAS 2359-09-3 EINECS/ELINCS 219-100-2 Synonyms 5-t-Butyl isophthalic acid 5-t-Butyl-m-phthalic acid Empirical C12H14O4... 

Butyl titanate. See Tetrabutyl titanate Butyl a-toluate. See Butyl phenylacetate 4-t-Butyl toluene. See p-t-Butyl toluene p-t-Butyl toluene... 

Phenylethanamine. See a-Methylbenzylamine Phenylethane. See Ethylbenzene Phenylethanoic acid butyl ester. See Butyl phenylacetate... 

Butyl lactate Butyl laurate Butyl levulinate N-Butyl-2-methylbutyrate Butylparaben Butyl phenylacetate n-Butyl propionate Butyl salicylate Butyl stearate Butyl sulfide Butyl 10-undecenoate Butyl valerate n-Butyraldehyde n-Butyric acid Cadinene Camphene Caproic acid Caprylic alcohol Carvacrol Carvacryl ethyl ether Carveol 4-Carvomenthenol Carvone d-Carvone cis-Carvone oxide... 

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