Hydrochloric Acid → Benzoic Acid

Participants

Reaction Steps

Methyl 3-(2-(α-L-fucopyranosyloxy)phenyl)benzoate (0.44 g, 1.18 mmol) was dissolved in acetonitrile (8 ml) and treated with a solution of lithium hydroxide hydrate (60 mg, 1.41 mM, in 0.5 ml water) and the mixture was stirred overnight at room temperature. The mixture was then treated with 2N HCl to pH 3 to 4 and the volatiles were removed under reduced pressure. The residue was purified by HPLC (reverse-phase, gradient elution 5-50% acetonitrile in water, 0.1% trifluoroacetic acid, monitored at 254 nm) which gave 3-(2-α-L-fucopyranosyloxy)phenyl)benzoic acid (174 mg, 40%) as a white solid, m.p.: 92°-93° C.; 1H NMR (300 MHz, DMSO-d6): 8.07 (s, 1H), 7.88 (t, J=8.7, 2H),7.51 (t, J=7.7, 1H), 7.29-7.43 (comp, 2H), 7.27 (d, J=8, 1H), 7.09 (t, J=7.2, 1H), 5.49 (d, J=3, 1H), 3.05-3.90 (comp, 7H), 0.97 (d, J=6, 3H); IR (KBr): 3402, 2932, 1695, 1498, 1457, 1219, 1076, 960, 838, 750; analysis: calculated for C19H20O7.0.3[CF3CO2H].0.2[H2O]: 59.1% C; 5.2% H. found: 59.1% C; 5.5% H.

Provenance & Evidence