Toluene → Benzoic acid, 4-nitro-, 2-ethylhexyl ester

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Reaction Steps

To a flask equipped with a magnetic stirrer, reflux condenser, and a nitrogen inlet was added 4-nitrobenzoyl chloride (53.0 grams, 0.285 moles), 2-ethylhexanol (28.6 grams, 0.22 moles), triethyl amine (30.2 grams, 0.30 moles) and 4-dimethylaminopyridine (6.98 grams, 0.0.57 moles) and anhydrous toluene (420 ml). The contents of the flask were heated at reflux for 16 hours; cooled to room temperature. It was diluted with diethyl ether (300 ml). The ether extract was washed with diluted HCl(1wt %, 3×100 ml), followed with a saturated sodium bicarbonate solution (3×100 ml), brine (3×100 ml), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to yield 57.2 grams of crude product as a yellow oil. 1H NMR (CDCl3) δ 8.3(d, 2H), 8.2(d, 2H), 4.3(d, 2H), 1.75(heptet, 1H), 1.2-1.6(m, 8H), 0.8-1.0(m, 6H).

Provenance & Evidence