Methyl bromoacetate → p-Decyloxybenzoyloxy acetic acid methyl ester

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Reaction Steps

Following the addition of 11.2 g (73 mMols) of bromoacetic acid methyl ester, a suspension of 20 g (67 mMols) of p-decyloxybenzoic acid, sodium salt, in 100 ml of methanol was heated for 3 hours and, after the addition of another 2 ml of bromoacetic acid methyl ester, for another 1.5 hours to boiling temperature. After the volatile constituents had been distilled off, the residue was extracted cold with methylene chloride, the solution was washed with water, concentrated by evaporation, the oily residue was taken up in petroleum ether, the solution was treated with active carbon and then reconcentrated by evaporation. p-decyloxybenzoyloxy acetic acid methyl ester melting at 30° to 32° C. was obtained in a yield of 15.8 g (68%). Purification by column chromatography (SiO2, Merck/methylene chloride:toluene=7:3) produced pure ester melting at 32.5° to 34° C.

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