Water → HCID 136335114, compound

Participants

Reaction Steps

To a solution of 4-{(benzyloxy)[(benzyloxy)imino]methyl}phenyl acetate (19) (1.671 g, 4.45 mmol) in dry methanol (30 ml) 3.43 N sodium methoxide solution in methanol (1.3 ml, 4.46 mmol) was added and the reaction mixture was stirred at ambient temperature until the starting material disappeared (ca. 1 hour). The mixture was poured into a mixture of water (60 ml) and saturated NaH2PO4 (30 ml), and extracted with ethyl acetate (2×25 ml). The extract was washed with brine (30 ml) and dried (Na2SO4). The solvent was evaporated and the residue was chromatographed on silicagel (50 g) with benzene-ethyl acetate (9:1) as eluent to give benzyl N-(benzyloxy)-4-hydroxybenzenecarboximidoate (15) (1.428 g, 96%) as an interchangeable mixture (2D TLC) of 2 isomers with Rf 0.62 and Rf 0.49 (toluene-ethyl acetate, 9:1). Major (less polar) isomer of 15: 1H NMR (DMSO-d6, HMDSO) δ: 4.99 (2H, s); 5.09 (2H, s); 6.80 (2H, d, J=8.7 Hz); 7.27-7.53 (10H, m); 7.67 (2H, d, J=8.7 Hz); 9.96 (1H, s). Minor (more polar) isomer of 15: 1H NMR (DMSO-d6, HMDSO) δ: 5.06 (2H, s); 5.24 (2H, s); 6.75 (2H, d, J=8.6 Hz); 7.27-7.53 (10H, m); 7.67 (2H, d, J=8.6 Hz); 9.84 (1H, s).

Provenance & Evidence