Hydroquinone → 4-(4-Hydroxy-phenoxy)-butyric acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-hydroxyphenol (3.3 g, 30 mmol) in ethanol (60 mL) was added K2CO3 (6.21 g, 45 mmol), Bu4NI (1.11 g, 3 mmol), and ethyl 4-bromobutanoate (4.68 g, 24 mmol). The resulting mixture was stirred at 60° C. overnight and filtered. To the filtrate was added water, and extracted with ethyl acetate, washed with brine, dried over Na2SO4 and concentrated. The residue was purified by column chromatograph on silica gel (ethyl acetate in petroleum ether, 10% v/v) to afford title product 0112-54 (1.6 g, 30%) as a brown solid. LCMS: 247 [M+23]+. 1H NMR (400 MHz, DMSO-d6): δ 1.26 (t, J=7.2 Hz, 3H), 2.08 (m, 2H), 2.51 (t, J=7.2 Hz, 2H), 3.93 (t, J=6.0 Hz, 2H), 4.15 (q, J=7.2 Hz, 2H), 6.75 (s, 4H).

Provenance & Evidence