Hydrochloric Acid → Methyl 5-Methoxy-2-methylbenzoate

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12.6 g of a 28% sodium methylate methanol solution and 4.2 g of copper iodide were added to 5 g of methyl 4-bromo-toluate dissolved in 20 ml of dimethylformamide and the mixture was refluxed under heating for 2 hours. The reaction mixture was adjusted to about pH 2 by adding 1N-hydrochloric acid thereto and extracted with ethyl acetate. and the organic layer was washed with a saturated saline solution and then dried over anhydrous sodium sulfate. The residue obtained by removing the solvent was applied to silica gel column chromatography to obtain 2.47 g of the title compound.

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