Phase-transfer-catalyzed synthesis of butyl 4-methoxyphenylacetate and its simultaneous hydrolysis by potassium hydroxide in oil-water biphasic system
Herein, we report for the first time simultaneous hydrolysis during the phase-transfer-catalyzed synthesis of butyl 4-methoxyphenylacetate using potassium hydroxide in biphasic medium. Effect of operating parameters on the reaction is presented. The yield of ester increases with the increase in the agitation speed up to 500 rpm and above that the conversion is not influenced by the agitation speed. At higher concentration of base, the hydrolysis product is more favored. Lower temperature and larger volume of water favors the esterfication. At high concentration of catalyst, sharp decrease in the yield of the ester is noticed. In the presence of highly polar solvents, the conversion of ester increases initially and then there was a sharp decrease. Rational explanations to account for the phenomena based on the results are made.
Design and synthesis of 4-methoxyphenylacetic acid esters as 15-lipoxygenase inhibitors and SAR comparative studies of them
A group of 4-methoxyphenylacetic acid esters were designed, synthesized and evaluated as potential inhibitors of soybean 15-lipoxygenase (SLO) on the basis of eugenol and esteragol structures. Compounds 7d-e showed the best IC50 in SLO inhibition (IC50 = 3.8 and 1.9 μM, respectively). All compounds were docked in SLO active site and showed that carbonyl group of compounds is oriented toward the FeIII-OH moiety in the active site of enzyme and fixed by hydrogen bonding with hydroxyl group. It is assumed that lipophilic interaction of ligand-enzyme would be in charge of inhibiting the enzyme activity. The selectivity of the synthetic esters in inhibiting of 15-HLOb was also compared with 15-HLOa by molecular modeling and multiple alignment techniques.
Sadeghian, Hamid,Attaran, Neda,Jafari, Zeinab,Saberi, Mohammad Reza,Pordel, Mehdi,Riazi, Mohammad Mahdi
experimental part
p. 2327 - 2335
(2009/09/08)
RHODIUM(I) CATALYZED CARBONYLATION REACTIONS OF HALIDES AND ETHERS
Benzylic bromides and methyl ioide react with ethers, carbon monoxide, potassium iodide, and the dimer of chloro(1,5-hexadiene)rhodium(I) to give esters in good yields.
Buchan, Caroline,Hamel, Nathalie,Woell, James B.,Alper, Howard
p. 5743 - 5746
(2007/10/02)
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