Isovanillin → HCID 24704043, compound

Participants

Reaction Steps

Isovanillin (0.95 g, 6.2 mmol) was alkylated with but-3-ynyl 4-methylbenzenesulfonate (2.1 g, 9.4 mmol) according to Procedure 4. The crude product was recystallised from EtOAc/petrol to provide 3-(but-3-ynyloxy)-4-methoxybenzaldehyde (0.44 g, 35%) as a colourless crystalline solid; mp 63-65° C.; δH (400 MHz, CDCl3) 2.06 (t, J=2.8 Hz, 1H, C≡CH), 2.76 (td, J=7.2, 2.8 Hz, 2H, CH2C≡CH), 3.96 (s, 3H, OCH3), 4.22 (t, J=7.2 Hz, 2H, OCH2), 6.99 (d, J5,6=8.0 Hz, 1H, H5), 7.43 (d, J2,6=1.4 Hz, 1H, H2), 7.45 (dd, J5,6=8.0, J2,6=1.4 Hz, 1H, H6), 9.85 (s, 1H, CHO); δC (100 MHz, CDCl3) 19.4, 56.2, 67.0, 70.3, 79.8, 110.9, 111.2, 127.1, 130.1, 148.4, 154.9, 190.7; vmax 1015, 1124, 1231, 1586, 1675, 2821, 3305 cm−1.

Provenance & Evidence