Benzylbenzoate

The enhanced reaction in ethanol is attributed to weakening of the tight, intramolecular hydrogen bond which is believed to facilitate photoenolization of 2-hydroxybenzophenone. t>-Hydroxybutyrophenone undergoes photoenolization in preference to Type II cleavage.25 The enol of o-benzylbenzo-phenone (2) forms a Diels-Alder adduct with dimethyl acetylenedicarboxylate, indicating that reaction with a reactive substrate is possible.30... 

Benzylbenzoate and derivs 2 B9S benzyl mononitrobenzoate 2 B9S dinitrobenzyl benzoate 2 B9S benzoate 2 B9S... 

Such regioselectivities are unique and suggest that redox pillared clays may have broad scope and utility as selective, heterogeneous catalysts for liquid phase oxidations. Indeed, V-PILC also catalyzes the oxidation of benzyl alcohol (to a mixture of benzoic acid and benzylbenzoate) whilst a-methyl benzylalcohol is left completely untouched.71 Similarly, p-substituted benzyl alcohols are oxidized whilst o-substituted benzyl alcohols are inert.71... 

Benzylbenzo[i>]thiophene13z and 2-p-methoxybenzylbenzo[i>]-thiophene and its 3-ethyl derivative 464 may be prepared by treating 2-benzo[6]thienyllithium or its 3-ethyl derivative with benzyl chloride or anisyl chloride, respectively. Various p-methoxybenzyl-benzo [6]thiophenes may be prepared by Friedel-Crafts reactions between the appropriate benzo[6]thiophene and anisyl chloride.464... 

The only cases of cyclization of 7-2-naphthylbutyric acids in which the ring does not close into the reactive 1-position to form a phenanthrene derivative are those in which either this position is blocked or the 8-position is substituted. The latter clearly seems to be an example of hindrance. An illustration is afforded by the cyclization of 7-8-methyl-2-naphthylbutyric acid (XXXIX) to the linear anthracene derivative XLI instead of the expected ketotetrahydrophenanthrene.26 The orientation influence of the methyl substituent would not be expected to affect the course of the reaction in such a manner. In like manner the tetramethyl derivative XL gave the product of linear ring closure XLII in good yield.27 A similar abnormal course of cyclization 28 has been observed in the benzylbenzoic acid derivative, o-(8-methyl-2-naphthyl- ... 

As much as 67 g. of 7 2-naphthylbutyric acid, using 500 g. of hydrogen fluoride, has been cyclized at one time.186 The yield of pure ketone was 94%. The method also is applicable to the cyclization of o-benzylbenzoic acids to anthrones.129... 

The excellent method for cyclizing o-benzylbenzoic acids to anthranol acetates, by heating the acid in- a mixture of acetic acid, and anhydride with zinc chloride as a catalyst,228 has been used also in the preparation of cyclic ketones of the tetralone type. In this way 7-3-acenaphthylbuty-ric acid has been cyclized in 78% yield 224 Y-2-phenanthrylbutyric acid48 and the 9,10-dihydro derivative97 in 51% and 59% yields respectively and a,j8-dimethyl-Y-2-naphthylbutyric acid in 90% yield.186... 

Another reagent, fused zinc chloride, which has been more commonly used for the ring closure of o-benzylbenzoic acids, was applied to the cyclization of 7-3-pyrenylbutyric acid (Table IY, example 2). The reaction was carried out at 180°, and the yield was 16%. 

D AURIA, J. C., CHEN, F., PICHERSKY, E., Characterization of an acyltransferase capable of synthesizing benzylbenzoate and other volatile esters in flowers and damaged leaves of Clarkia breweri., Plant Physiol., 2002,130,466-476. 

Oil Monomers Organic solvents Surfactants Miglyol, Lipiodol, benzylbenzoate Ethylcyanoacrylate, isobutylcyanoacrylate, K-butylcyanoacrylate, isohexylcyanoacrylate Ethanol, acetone, acetonitrile, K-butanol, isopropanol Poloxamer 188, poloxamer 238, poloxamer 407, Triton X100, Tween 80... 

Two types of 3-benzoylbenzo[7]furans were regioselectively prepared from their corresponding starting materials 2-methylbenzo[ ]furan and 2-benzylbenzo[7]furan through a Friedel-Crafts reaction pathway, as shown in Scheme 47 <2002JME623>. 

The polyphosphoric acid (PPA)-catalyzed cyclocondensation of ketone 79 gave the 3-aryl-2-benzylbenzo[. ]seleno-phene 80 (Scheme 8) <1994JCM98>. The latter was converted into derivative 81 which was evaluated as a ligand for antiestrogenic binding sites. 

C14H11CI 1-chloro-2-(trans-2-phenylvmyl)benzene 1657-52-9 25.00 1.1496 2 26946 C14H1202 2-benzylbenzoic acid 612-35-1 21.50 1.2062 2... 

Suggest syntheses of the following compounds from the starting material given (a) 4-chloro-3-nitrobenzoic acid from toluene (b) 2-chloro-4-nitrobenzoic acid from toluene (c) 4-benzylbenzoic acid from toluene (d) l-ethyl-3-nitrobenzene from benzene (e) isobutylbenzene from benzene. 

Partial oxidation of benzyl alcohol has been studied in detail. Benzyl alcohol undergoes dehydration to dibenzyl ether and water, disproportionation to benzaldehyde and toluene over alumina and other acid catalysts [2] whereas it undergoes dehydrogenation on metal oxides to yield benzaldehyde and toluene as major products and benzylbenzoate, benzene and methanol in small amounts depending upon the reaction conditions [10]. The various products formed as a result of catalytic decomposition may be represented as... 

The effect of temperature on conversion and selectivity in benzyl alcohol dehydrogenation in the presence of oxygen is shown in the Fig, 5 The selectivity of benzaldehyde decreases with temperature, whereas that of toluene increases. At high temperatures small amounts of benzoic acid and benzylbenzoate is also observed. The selectivity of which increases with increase in temperature. 

The effect of contact time on conversion and selectivity in the presence of oxygen is shown in Fig.6. Conversion increases with increase in contact time. Selectivity to benzaldehyde decreases with increase in contact time which is in contrast to what is observed in absence of oxygen. On the other hand the selectivity to benzoic acid and benzylbenzoate increases with increase in contact time. Therefore it can be suggested that at higher contact time, benzaldehyde formed gets oxidised to benzoic acid, which in turn condenses with a molecule of benzyl alcohol to form benzylbenzoate. The mechanism proposed is as shown in scheme 1. 

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