3-Nitrobenzaldehyde → Diethyl P-[hydroxy(3-nitrophenyl)methyl]phosphonate

Participants

Reaction Steps

m-Nitrobenzaldehyde (4.53 g, 30 mmol) was dissolved in diethyl phosphite (4.14 g, 30 mmol) under gentle heating. The solution was brought to room temperature and KF (8.7 g, 0.15 mole) was added with rapid stirring. After 30 min the mixture was suspended in CH2Cl2 (150 ml). The resultant suspension was filtered and the filtrate was concentrated under reduced pressure furnishing 8.57 g (99%) of 17 as a yellow colored solid, mp 93-95° C., IR (neat): 3750-3040, 1540, 1355, 1205 and 1050; 1H NMR (200 MHz, CDCl3): δ1.23 (6H, m), 4.10 (4H, m), 5.14 (1H, d, J=12 Hz), 5.94 (1H, s, OH) and 7.93 (4H, m); 13C NMR (50 MHz, CDCl3): δ17.6, 64.2, 64.9, 72.1, 122.4, 123.1, 129.3, 133.4, 139.8 and 148.3; HR-MS (EI): m/e 289.0715 (M+C11H16NO6P requires 289.0714).

Provenance & Evidence