Reaction Steps
p-Hydroxybenzaldehyde (0.37 g, 3.0 mmol), 8 (1.2 g, 3.0 mmol), and DMAP (0.04 g, 0.3 mmol) were dissolved in 300 mL of CH2Cl2. DCC (1.24 g, 6.0 mmol) was added to reaction flask which was stirred at room temperature for three days. The solvent was removed under reduced pressure, and the residue purified using column chromatography (CH2Cl2:EtOH, 10:0.05). The product was then recrystallized from ethanol. Yield 0.3 g (20%). 1HNMR: δH (CDCl3; 300 MHz): 1.24-1.52 (15 H, m, CH2/O—CH2—CH3), 1.69 (2 H, m, S—CH2—CH2), 1.81 (2 H, m, O—CH2—CH2), 3.11 (2 H, t, 3J=7.3 Hz, SCH2), 4.02 (2 H, t, 3J=6.5 Hz, O—CH2), 4.65 (2 H, q, 3J=7.1 Hz, O—CH2—CH3), 6.99 (2 H, d, 3J=8.9 Hz, Ar—H), 7.40 (2 H, d, 3J=8.5 Hz, Ar—H), 7.96 (2 H, d, 3J=8.6 Hz, Ar—H), 8.14 (2 H, d, 3J=8.9 Hz, Ar—H), 10.0 (1 H, s, COH). 13C NMR: δC (CDCl3; 75 MHz): 13.8, 25.9, 28.1, 28.3, 28.8, 29.1, 29.3, 29.4, 35.9, 68.4, 69.7, 114.4, 120.8, 122.6, 131.2, 132.4, 133.9, 155.9.
