• Journal of the Korean Chemical Society
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• v.39 no.8
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• pp.657-665
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• 1995

The oxidation of various benzyl ethers and benzyl alkyl ethers to benzoates has been studied in two-phase system of $CH_3CO_2Et$ and aqueous NaOCl (6.6 mol eq.). The oxidant N-oxo-4-methoxy-2,2,6,6-tetramethylpiperidium bromide (N-oxoammonium salt) was prepared in situ and recycled by addition of 4-methoxy-2,2,6,6-tetramethylpiperidine-1-oxyl (0.03 mol eq., 4-methoxy-TEMPO), co-catalyst KBr (0.03mol eq.) and second oxidant NaOCl. Thus the catalytic amount of 4-methoxy-TEMPO was used. An adjustment of the pH value of below 8.0 was also required for this reaction with 2.5 hr of reaction time at 0∼5$^{\circ}C$. Under these conditions benzyl ethers were oxidized to benzoates. The selectivity of oxidation of benzyl alkyl ethers is dependent on the acidity of hydrogen and steric effect of alkyl group.

• Archives of Pharmacal Research
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• v.28 no.1
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• pp.49-54
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• 2005

The chromatographic separation of the hexane soluble fraction of the methanol extract of the aerial parts of Solidago virga-aurea var. gigantea Mo. (Compositae) led to the isolation of a new benzylbenzoate (1) together with four known benzylbenzoates (2-5). Their structures were determined as 2-methoxybenzyl-2-hydroxybenzoate (1), benzyl-2-hydroxy-6-methoxy­benzoate (2), 2-methoxybenzyl-2,6-dimethoxybenzoate (3), 2-methoxybenzyl-2-methoxy-6­hydroxybenzoate (4), and benzyl-2,6-dimethoxybenzoate (5). Their structures were established by spectroscopic methods. Biological effects of compounds, 1 and 2, were investigated in vitro usingherapeutic agents by stimulating macrophage functions, with potential use in the treat­ mouse peritoneal macrophages. The benzylbenzoates (1 and 2) could serve as immunotherapeutic agents by stimulating macrophage functions, with potential use in the treatment of infectious diseases.

• Journal of the Korean Chemical Society
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• v.35 no.1
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• pp.90-95
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• 1991

A method for the selective syntheses of alkyl (alkoxymethyl)benzoates from halobenzyl halides by two steps in one pot process is described. In the first step, benzyl halide moiety is etherified with alkoxide anion in alcohol by Williamson ether process. In the second step, aryl halide moiety is carbonylated to give alkyl (alkoxymethyl)benzoate with alcohol, Na$_2$CO$_3$, CH$_3$I, and carbon monoxide (1 atm) in the presence of a catalytic amount of Co$_2$(CO)$_8$ in excellent yield.