Diethyl Ether → Methyl 2-(2,4-di-tert-pentylphenoxy)-5-methoxymethylbenzoate

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Reaction Steps

To a solution of sodium hydride (1.2 g, 0.05 mol) in pyridine (60 mL), was added a solution of 2,4-di-tert-pentylphenol (12.9 g, 0.055 mol) in pyridine (20 mL) with stirring. Gas evolution ceased in approximately 1.5 hr at which time methyl 2-bromo-5-methoxylbenzoate was added. Copper (I) chloride (1.24 g, 0.0126 mol) was added and the mixture heated to reflux for 8 hours. The reaction mixture was diluted with diethyl ether (100 mL) and washed with 3N HCl (3×50 mL) and then washed with saturated sodium bicarbonate (1×50 mL). The organic extracts were dried over sodium sulfate, filtered and concentrated to give a dark oil. Chromatography on silica gel with 1:1 heptane:ethyl acetate yielded the pure product as a viscous oil in 90% yield. NMR and mass spectral analysis were consistent with proposed structure.

Provenance & Evidence