Hydrochloric Acid → N-{4-[2-(3,4-dihydroxyphenyl)-trans-vinyl]benzenesulfonyl}-morpholine

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Reaction Steps

N{4-[2-(3,4-Di(methoxymethoxy)phenyl)-trans-vinyl]benzenesulfonyl} morpholine (0.6 g, 1.3347 mmol) was dissolved in a mixed solvent of MeOH (100 mL) and CH2Cl2 (60 mL). The homogeneous solution was bubbled with argon gas. Water (0.2 g, 11.11 mmol) and concentrated hydrochloric acid (0.9 mL, 10.8 mmol) were added and stirred for 45 hours. The solvents were removed by evaporation and the solid residue was washed with water for several times. The solid was dried under high vacuum in the presence of Drierite providing 0.4388 g of N-{4-[2-(3,4-dihydroxyphenyl)-trans-vinyl]benzenesulfonyl}-morpholine as a yellowish solid (1.214 mmol, yield 91.0%). 1H NMR (Acetone-D6 and DMSO-d6, 300.16 MHz) δ (ppm) 9.05 & 9.03 (2s, 0.64H), 8.81 & 8.79 (2s, 0.65H), 7.81 (d, J=8.5 Hz, 2H), 7.71 (d, J=8.3 Hz, 2H), 7.32 (d, J=16.3 Hz, 1H), 7.13-7.04 (m, 2H), 6.96 (dd, J=8.2 & 1.9 Hz, 1H), 6.80 (d, J=8.3 Hz, 1H), 3.68-3.65 (m, 4H) and 2.94-2.91 (m, 4H). MS (ESI) m/z: 362 (M+1)+, 384 (M+23)+ and 745 (2M+23)+.

Provenance & Evidence