Synthesis
The general procedure for the synthesis of 4-methoxypyridin-2-aldehyde from (4-methoxypyridin-2-yl)methanol was as follows:
- Manganese(IV) oxide (2.412 mL, 139.42 mmol, 4 eq.) was added batchwise to a solution of (4-methoxypyridin-2-yl)methanol (4.85 g, 34.85 mmol, 1 eq.) in ethyl acetate (150 mL).
- The reaction mixture was stirred at 80 °C for 2 hours.
- Upon completion of the reaction, the hot reaction mixture was filtered through diatomaceous earth.
- The filtrate was evaporated to dryness to afford the target product 4-methoxypyridine-2-aldehyde (3.01 g, 21.93 mmol, 62.9% yield).
1H NMR (400.132 MHz, DMSO) δ 3.93 (3H, s), 7.27 (1H, m), 7.44 (1H, d), 8.63 (1H, d), 9.96 (1H, s).
References
[1] Patent: WO2009/56886, 2009, A1. Location in patent: Page/Page column 54
[2] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458
[3] Inorganic Chemistry, 2013, vol. 52, # 11, p. 6481 - 6501
[4] Bulletin of the Chemical Society of Japan, 2015, vol. 88, # 6, p. 784 - 791
[5] Yakugaku Zasshi, 1957, vol. 77, p. 11,13
