Phenyl butyl acetate

The 7t systems of aromatic rings can act as neighboring groups. The reactions of the 3-phenyl-2-butyl tosylates are good examples. D. J. Cram [1919-2001, awarded the Nobel Prize in Chemistry in 1987 for work on crown ethers (p. 254)] and his co-workers showed that in acetic acid, the optically active 3-phenyl-2-butyl tosy-late shown in Figure 21.23 gives a racemic mixture of the corresponding 3-phenyl-2-butyl acetates. 

Successful results have been obtained (Renfrew and Chaney, 1946) with ethyl formate methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec.-butyl and iso-amyl acetat ethyleneglycol diacetate ethyl monochloro- and trichloro-acetates methyl, n-propyl, n-octyl and n-dodecyl propionates ethyl butyrate n-butyl and n-amyl valerates ethyl laurate ethyl lactate ethyl acetoacetate diethyl carbonate dimethyl and diethyl oxalates diethyl malonate diethyl adipate di-n-butyl tartrate ethyl phenylacetate methyl and ethyl benzoates methyl and ethyl salicylates diethyl and di-n-butyl phthalates. The method fails for vinyl acetate, ieri.-butyl acetate, n-octadecyl propionate, ethyl and >i-butyl stearate, phenyl, benzyl- and guaicol-acetate, methyl and ethyl cinnamate, diethyl sulphate and ethyl p-aminobenzoate. 

On the other hand, 3-phenylpropionitrile was synthesized from Z-3-phenyl-propionaldoxime (0.75 M) in a quantitative yield (98gP ) by the use of cells of E. coli JM 109/pOxD-9OF, a transformant harboring a gene for a new enzyme, phenylacetaldoxime dehydratase, from Bacillus sp. strain OxB-1. Other arylalkyl- and alkyl-nitriles were also synthesized in high yields from the corresponding aldoximes. Moreover, 3-phenylpropionitrile was successfully synthesized by the recombinant cells in 70 and 100% yields from 0.1 M unpurified P/Z-3-phenylpropionaldoxime, which is spontaneously formed from 3-phenylpropionaldehyde and hydroxylamine in a butyl acetate/water biphasic system and aqueous phase, respectively. 

The initial study of the La3 +-catalyzed methanolysis of carboxylate esters163 reported the apparent second-order rate constant for La2 + ( OCH3)2-catalyzed methanolysis of some representative examples of aryl esters (2, 5 and 2,4-dinitrophenyl acetate (14)), phenyl benzoate (15) and three aliphatic esters, ethyl acetate, isopropyl acetate (16) and tert-butyl acetate (17). Given in Table 6 are the rate constants for the La3+ and methoxide-catalyzed methanolysis of these esters along with... 

Phenyl /-butyl ether, 46, 89 /3-Phenylcinnamic acid, from benzo-phenone and triethyl phosphono-acetate, 48, 75... 

AI3-00040, see Cyclohexanol AI3-00041, see Cyclohexanone AI3-00045, see Diacetone alcohol AI3-00046, see Isophorone AI3-00050, see 1,4-Dichlorobenzene AI3-00052, see Trichloroethylene AI3-00053, see 1,2-Dichlorobenzene AI3-00054, see Acrylonitrile AI3-00072, see Hydroquinone AI3-00075, see p-Chloro-rrr-cresol AI3-00078, see 2,4-Dichlorophenol AI3-00085, see 1-Naphthylamine AI3-00100, see Nitroethane AI3-00105, see Anthracene AI3-00109, see 2-Nitropropane AI3-00111, see Nitromethane AI3-00118, see ferf-Butylbenzene AI3-00119, see Butylbenzene AI3-00121, see sec-Butylbenzene AI3-00124, see 4-Aminobiphenyl AI3-00128, see Acenaphthene AI3-00134, see Pentachlorophenol AI3-00137, see 2-Methylphenol AI3-00140, see Benzidine AI3-00142, see 2,4,6-Trichlorophenol AI3-00150, see 4-Methylphenol AI3-00154, see 4,6-Dinitro-o-cresol AI3-00262, see Dimethyl phthalate AI3-00278, see Naphthalene AI3-00283, see Di-rj-butyl phthalate AI3-00327, see Acetonitrile AI3-00329, see Diethyl phthalate AI3-00399, see Tributyl phosphate AI3-00404, see Ethyl acetate AI3-00405, see 1-Butanol AI3-00406, see Butyl acetate AI3-00407, see Ethyl formate AI3-00408, see Methyl formate AI3-00409, see Methanol AI3-00520, see Tri-ocresyl phosphate AI3-00576, see Isoamyl acetate AI3-00633, see Hexachloroethane AI3-00635, see 4-Nitrobiphenyl AI3-00698, see IV-Nitrosodiphenylamine AI3-00710, see p-Phenylenediamine AI3-00749, see Phenyl ether AI3-00790, see Phenanthrene AI3-00808, see Benzene AI3-00867, see Chrysene AI3-00987, see Thiram AI3-01021, see 4-Chlorophenyl phenyl ether AI3-01055, see 1.4-Dioxane AI3-01171, see Furfuryl alcohol AI3-01229, see 4-Methyl-2-pentanone AI3-01230, see 2-Heptanone AI3-01231, see Morpholine AI3-01236, see 2-Ethoxyethanol AI3-01238, see Acetone AI3-01239, see Nitrobenzene AI3-01240, see I idine AI3-01256, see Decahydronaphthalene AI3-01288, see ferf-Butyl alcohol AI3-01445, see Bis(2-chloroethoxy)methane AI3-01501, see 2,4-Toluene diisocyanate AI3-01506, see p,p -DDT AI3-01535, see 2,4-Dinitrophenol AI3-01537, see 2-Chloronaphthalene... 

Schugerl 115] has recently furnished a detail analysis of the reactive extraction of penicdlin-G and V and precursors like phenyl and phenoxy acetic acids. Thirty different amines have been studied for reactive extraction of penicillins 116] in various solvents such as butyl acetate, chloroform, di-isopropyl ether, kerosene, dioctyl ether, etc. Tertiary amines in n-butyl acetate were found to be advantageous because of their low reactivity with solvent but the distribution coefficients of their complexes are significantly lower than those of secondary amines. While using quaternary ammonium salts for ion-exchange extraction, re-extraction is difficult and very large amounts of anion (e.g.. Cl ) are needed to recover penicillins. The basic relationship for distribution coefficient and extraction kinetics have now been fairly developed for amine-penicillin systems. 

Facilitated transport of penicilHn-G in a SLM system using tetrabutyl ammonium hydrogen sulfate and various amines as carriers and dichloromethane, butyl acetate, etc., as the solvents has been reported [57,58]. Tertiary and secondary amines were found to be more efficient carriers in view of their easy accessibility for back extraction, the extraction being faciUtated by co-transport of a proton. The effects of flow rates, carrier concentrations, initial penicilHn-G concentration, and pH of feed and stripping phases on transport rate of penicillin-G was investigated. Under optimized pH conditions, i. e., extraction at pH 6.0-6.5 and re-extraction at pH 7.0, no decomposition of peniciUin-G occurred. The same SLM system has been applied for selective separation of penicilHn-G from a mixture containing phenyl acetic acid with a maximum separation factor of 1.8 under a liquid membrane diffusion controlled mechanism [59]. Tsikas et al. [60] studied the combined extraction of peniciUin-G and enzymatic hydrolysis of 6-aminopenicillanic acid (6-APA) in a hollow fiber carrier (Amberlite LA-2) mediated SLM system. 

Phenyl-1,3-butanedione, b64 4-Phenyk < c-butyl acetate, m361 Phenyl Cellosolve, p72 Phenyl chloride, c41... 

Tazanolast. Oxo[[3-(177-tetrazol-5-yl)phenyl]amino]acetic acid butyl ester 610, antiallergic, antiasthmatic. Pranlukast. V-[4-Oxo-2-(17/-tetrazol-5-yl)-477-l-benzopyran-8-yl]-4-(4-phenylbutoxy)benzamide 611, antiallergic. 

A solution of 561 mg of 2-[3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N-tert-butyl-decahydro-(4aS,8aS) -isoquinoline-3(S)-carboxamide and 372 mg of N-(benzyloxycarbonyl)-L-asparagine in 20 ml of dry tetrahydrofuran was cooled in an ice/salt mixture. 189 mg of hydroxybenzotriazole, 161 mg of N-ethylmorpholine and 317 mg of dicyclohexylcarbodiimide were added and the mixture was stirred for 16 h. The mixture was then diluted with ethyl acetate and filtered. The filtrate was washed with aqueous sodium bicarbonate solution and sodium chloride solution. The solvent was removed by evaporation and the residue was chromatographed on silica gel using dichloromethane/methanol (9 1) for the elution to give 434 mg of 2-[3(S)-[[N-(benzyloxycarbonyl)-L-asparaginyl]amino]-2(R)-hydroxy-4-phenyl butyl]-N-tert-butyl-decahydro-(4aS,8aS)-isoquinoline-3(S)-carboxamide as a white solid from methanol/diethyl ether. 

The log (rate) vs. log (time) curves for the McLafferty rearrangement in the molecular ions of n-butyl acetate, 2-phenylethyl acetate, 2-phenyl-propyl acetate and 2-dimethylaminoethyl acetate have been found to be approximately parallel to each other and the rates at any time decreased significantly on going from n-butyl acetate to 2-phenylethyl acetate to... 

Butyl acetate gave butyl phenyl tellurium in 30% yield under similar conditions. 

The reference cited [5] also gives procedures for related magnesiations of other carboxylic acids, phenylacetronitrile, t-butyl acetate, acetophenone, methyl phenyl sulfone, and diethyl phenyl-methanephosphonate. 

Ans. (a) Butyl acetate or butyl ethanoate (b) Phenyl formate or phenyl methanoate... 

Genus, species Ethanol Ethyl acetate 3-Methyl- butyl acetate Ethyl octanoate 2-Methyl propanol 3-Methyl- butanol 2-Phenyl ethanol Acetic acid Acetaldehyde... 

SYNS ACETIC ACID, PHENYL-, BUTYL ESTER BENZENEACETIC ACID, BUTYL ESTER (9CI) BUTYL... 

Cl 3H1802 2-methyI-4-phenyl-2 butyl acetate 103-07-1 463.18 40,357 2 26405 C13H24 dicyclohexyl methane 3178-23-2 525.95 46,383 1,2... 

Fig. 4. Sedimentation coefficient (s) vs. molecular weight M - for ladder polysiloxanes 1 poly-phenylsiloxane in benzene ) 2 poly(phenyl-isohexylsiloxane) (1 1) in butyl acetate ...

In view of the fact that the methanol-phenyl isocyanate reaction is known to be an auto-catalytic reaction due to the weakly basic character of the phenylurethane formed, one would expect an upward drift of the second-order plot if the reaction were truly of the second order. This is apparently the case in n-butyl acetate and dioxane. The straight line plot in MEK and acetonitrile and the downward curvature found in toluene and nitrobenzene were taken to indicate an order greater than 2 with respect to the reactants. It appeared that the deviations from second-order kinetics toward higher order in the sequence toluene > nitrobenzene > acetonitrile > MEK > n-butyl acetate > dioxane increased with an increase in the hydrogen bonding capacity of the solvent. 

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