Hydrolysis of a dibromomethyl arene; 2-Hydroxyisophthalaldehyde
Submitted May 27, 2010, published May 27, 2010
David Fox (email@example.com
A contribution from
Fox Group, Warwick University
2,6-Bis(dibromomethyl)anisole (13.42 g, 30 mmol) was suspended in 90% HCHO(aq) (70 ml) and heated at reflux for 16 hours. The deep-red coloured solution was allowed to cool and was then poured into cold water (200 ml). The precipitate was collected via filtration and then recrystallised from water to give 2,6-diformylphenol as white crystals (2.70g, 60%).
mp 124 oC (ref 123 oC); νmax (KBr)/cm-1 3436 (OH), 1681 (C=O); δH (200MHz, CDCl3) 11.68 (1H, s, OH), 10.26 (2H, s, CHO), 7.98 (2H, d, J 8.0, m-CH), 7.15 (1H, t, J 8.0, p-CH); m/z (APCI-) 149 (100%, (M-H)-).
S. Labidalle, E. Jean, H. Moskowitz, M. Miocque and C. Thal, Tetrahedron Lett., 1981, 22, 2869-2870