Diethyl Ether → N,N-diethyl-4-hydroxybenzamide

Participants

Reaction Steps

A solution of n-butyl lithium in hexane (1.6M, 22.87 ml) was added to a solution of diethylamine (3.74 ml) in dry tetrahydrofuran (100 ml), at ambient temperature and under an atmosphere of argon. The reaction mixture was stirred for 15 minutes. Ethyl 4-hydroxybenzoate (5 g) was then added and the reaction mixture stirred for 16 hours. Diethyl ether was added to the reaction mixture and the mixture was washed with water, dried (MgSO4) and evaporated. The residue was purified by flash column chromatography on silica gel (Merck Art No. 9385) using a 1:3 (v/v) mixture of ethyl acetate/hexane as eluent to give 4-hydroxy-N,N-diethyl benzamide as a solid (1.17 g), m.p. 122.5° C.; NMR ([CD3 ]2SO): 1.1-1.15(6H,t), 3.2-3.4(4H,m), 6.75-6.85(2H,d), 7.15-7.25(2H,d), and 9.7(1H,s); m/z 194(M+H).

Provenance & Evidence