Catechol → Ethyl 4-(2-hydroxyphenoxy)butanoate

Participants

Reaction Conditions

Reaction Steps

To a solution of pyrocatechol (5.51 g, 50 mmol) in dry DMF (30 mL) was slowly added sodium hydride (1.2 g, 50 mmol) at 0° C. After stirring at 25° C. for 4 hours, the reaction mixture was heated at 65-70° C. for 1 hour followed by an addition of ethyl 4-bromobutyrate (10.7 mL, 75 mmol). The reaction mixture was then left stirring at this temperature for 6 hours. Upon quenching with water, extraction with dichloromethane, and evaporation gave the crude product which was purified by column chromatography, eluting with 87% hexane:10% CH2Cl2:3% EtOAc. Crystallization with hexane afforded a white solid in 55% yield (6.17 g, mp. 37.2-38.4° C.). 1H NMR (400 MHz, CDCl3): 1.26 (3H, t, J=7.1 Hz), 2.17 (2H, m), 2.52 (2H, t, J=7.0 Hz), 4.09 (2H, t, J=6.0 Hz), 4.16 (2H, q, J=7.1 Hz), 6.81-6.89 (3H, m), 6.92-6.94 (1H, m).

Provenance & Evidence