Methoxybenzyl acetate

When 3-methoxybenzyl acetate is photolyzed, however, the products expected from free radical coupling are decreased and a substantial amount of 3-methoxybenzylalcohol results. A carbonium ion intermediate has been proposed in the photolysis of this meta ester ... 

The pre/ivference for solvolysis of meta substituted esters such as m-nitro-phenyl phosphate and m-methoxybenzyl acetate was discovered by Havinga et and studied further by Zimmerman (equation 50). Radicals can be formed in these reactions, and there is some dispute as to whether radical pairs also lead to ion pairs (equation 50). ... 

Experimental agreement with the molecular orbital calculations was found (24) in the aqueous dioxane photolyses of 4-methoxybenzyl acetate (XXXVTI), 3-mcthoxybenzyl acetate (XXXVIII), and 3,5-dimethoxyhenzyl acetate (XXXIX). Under conditions where there was no observeablo dark reaction, these compounds underwent lieterolytic and liomolytic fission reactions. 4-Methoxybenzyl acetate gave, mainly... 

A mixture of 4-methoxybenzyl alcohol le (5 mmol) and acetic anhydride (5 mmol) in a beaker covered with watch glass was irradiated by microwaves for 10 min (heating and cooling at the interval of 1 min). After completion of die reaction (TLC), the product was extracted with ether (3x15 mL). The ether layer was washed with 10% NaOH and then dried with anhydrous sodium sulfate. Removal of the solvent under reduced pressure gave 4-methoxybenzyl acetate 2e in excellent yield (95%). 

For a series of methylbenzenes, the rates decreased in the order toluene > xylenes > mesitylene > durene > hexamethylbenzene. This order of reactivity is the reverse of that expected for a mechanism involving electrophilic substitution or electron transfer. However, Bushweller598 found that electron-releasing groups facilitate the benzylic oxidation of substituted toluenes by Pd(OAc)2 in acetic acid. p-Methoxy toluene gave a 96% yield of p-methoxybenzyl acetate, and p-nitrotoluene gave only 2% p-nitrobenzyl acetate, in agreement with either an electrophilic substitution or electron transfer mechanism. More mechanistic studies are necessary to clear up these anomalies. Steric effects may play an important role in these reactions. 

Heating toluene with lead tetraacetate at 80 °C for 54 h gives only 25% of benzyl acetate, but ethylbenzene and anisole give 63% of a-meth-ylbenzyl acetate after 16 h and 60% of p-methoxybenzyl acetate after 3 h at 80 °C, respectively [437]. Under similar conditions, acenaphthene yields... 

Benzylic oxidation of toluenes. Toluene is oxidized by palladium acetate (equimolar) in acetic acid at 90° (13 hrs.) to benzyl acetate (80% yield), benzaldehyde (4%) and benzylidene diacetate (6%) with formation of palladium (O).4 This oxidation is sensitive to electronic factors. Thus p-methoxytoluene is converted in 96% yield into p-methoxybenzyl acetate whereas p-nitrotoluene is essentially inactive. 

In a third variant on this theme, methyl 3,4,6-tri-O-benzyl-l-thio-a-D-mannopyranoside is converted into a p-methoxybenzyl acetal by first etherifying the 2-OH group with p-methoxyben/yl bromide and then treating the resulting p-methoxybenzyl ether with a hydroxyl compound in the presence of 2,3 -dichloro-5,6-dicyano-l,4-benzoquinone (DDQ). Activation of the methylthio anomeric center with methyl triflate then produces the (3-D-mannopyranoside as the only possible glycoside, again because of the acceptor being tethered to the (3 side of the mannopyranoside.56... 

Synonyms Acetic acid 4-methoxybenzyl ester 4-Methoxybenzyl acetate p-Methoxybenzyl acetate... 

Methoxybenzyl acetate p-M ethoxy benzyl acetate. See p-Anisyl acetate 4-Methoxybenzylacetone. See 4-p-Methoxyphenyl-2-butanone 2-Methoxybenzyl alcohol. See o-Anisyl alcohol 4-Methoxybenzyl alcohol. See p-Anisyl alcohol 4-Methoxybenzyl alcohol (o-, m-, p-). See Anisyl alcohol... 

Ethoxy-3-methoxybenzyl acetate 4-Ethoxy 3-methoxybenzyl benzoate... 

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