Ethanol → Ethyl [4-(methylsulfanyl)phenyl]acetate

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Reaction Steps

To a solution of 4-methylthiophenylacetic acid (1.0 g, 5.48 mmol) in 55 mL of ethanol was slowly added a catalytic amount of concentrated sulfuric acid. The mixture was stirred at room temperature overnight and then concentrated at reduced pressure. The residue was partitioned between methylene chloride and sodium bicarbonate. The organic layer was washed with brine, dried with magnesium sulfate, filtered, and concentrated to yield 1.1 g of a colorless oil (96%). 1H NMR (300 MHz, CDCl3) δ7.22 (s, 4H), 4.15 (q, J=6 Hz, 2H), 3.57 (s, 2H), 2.47 (s, 3H), 1.25 (t, J=6 Hz, 3H).

Provenance & Evidence