P-Cresol → Ethyl 2-(4-methylphenoxy)phenylacetate

Participants

Reaction Steps

p-Cresol (4.45 g) was added portionwise over 30 minutes to a stirred suspension of sodium hydride (60% dispersion in mineral oil; 1.81 g) in N,N-dimethylformamide (DMF) (80 ml). When evolution of hydrogen ceased, ethyl-α-bromophenylacetate (10.0 g) was added and the mixture was left to stand for 20 hours. Water (500 ml) was added and the mixture was extracted with ethyl acetate (2×250 ml). The extracts were washed with water (250 ml), followed by saturated sodium chloride solution (250 ml) and then dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by flash chromatography, eluting with ethyl acetate/hexane (1:19 v/v), to give ethyl 2-(4-methylphenoxy)phenylacetate (B) (6.7 g), as an oil; NMR (d6 -DMSO): 1.2(t, 3H), 2.15(s, 3H), 4.1(q, 2H), 5.9(s, 1H), 7.2-7.6(m, 9H).

Provenance & Evidence