Reaction Steps
Synthesized as described above for compound 10. Quantities: 3 (12.0 g, 41.3 mmol), KOH (3.62 g, 64.7 mmol), oxalyl chloride (12 mL, 0.15 mol), p-hydroxybenzaldehyde (5.25 g, 43.0 mmol), triethylamine (35 mL, 0.25 mol), DMAP (0.25 g, 2.0 mmol). Yield 5.6 g (36%). 1H NMR: δH (CDCl3; 300 MHz): 1.27-1.57 (10 H, m, CH2), 1.85 (2 H, m, O—CH2—CH2), 2.07 (2 H, m, CH2═CH—CH2), 4.07 (2 H, t, 3J=6.6 Hz, O—CH2), 4.99 (2 H, m, CH2═CH), 5.84 (1 H, m, CH2═CH), 7.00 (2 H, d, 3J=9.0 Hz, Ar—H), 7.42 (2 H, d, 3J=8.5 Hz, Ar—H), 7.98 (2 H, d, 3J=8.6 Hz, Ar—H), 8.16 (2 H, d, 3J=9.0 Hz, Ar—H), 10.03 (1 H, s, COH). 13C NMR: δC (CDCl3; 75 MHz): 26.4, 29.3, 29.4, 29.5, 29.7, 29.8, 34.2, 68.8, 114.6, 114.8, 121.2, 123.0, 131.6, 132.8, 134.3, 139.5, 156.3, 164.3, 164.6, 191.4.
