Reaction Steps
Synthesized as described above for compound 10. Quantities: 4 (10.10 g, 33 mmol), KOH (2.46, 45 mmol), oxalyl chloride (13 mL, 148 mmol), p-hydroxybenzaldehyde (4.6 g, 38 mmol), triethylamine (33.7 mL, 0.24 mol), DMAP (0.20 g, 1.6 mmol). Yield 8.9 g (71%). 1HNMR: δH (CDCl3; 300 MHz): 1.24-1.52 (12 H, m, CH2), 1.83 (2 H, m, O—CH2—CH2), 2.04 (2 H, m, CH2═CH—CH2), 4.05 (2 H, t, 3J=6.5 Hz, O—CH2), 4.95 (2 H, m, CH2═CH), 5.82 (1 H, m, CH2═CH), 6.99 (2 H, d, 3J=9.0 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=9.0 Hz, Ar—H), 10.0 (1 H, s, COH). 13C NMR: δC (CDCl3; 75 MHz): 26.4, 29.3, 29.5, 29.5, 29.7, 29.8, 29.9, 34.2, 68.8, 114.6, 114.8, 121.2, 123.0, 131.6, 132.8, 134.3, 139.6, 156.3, 164.3, 164.6, 191.4.
