Hydrochloric Acid → (3-Methoxy-4-nitrobenzyl)phosphonic acid

Participants

Reaction Conditions

Reaction Steps

A suspension of diethyl (3-methoxy-4-nitrobenzyl)phosphonate (Compound 114E, 5.04 g, 16.6 mmol) in concentrated HCl (50.0 mL, 1630 mmol) was heated at 120° C. for a total of 16 h. After cooling to ambient temperature, the reaction mixture was concentrated in vacuo. After drying under vacuum for several hours, a solid had precipitated upon standing, giving the title material as a yellow solid, 4.1398 g (96%, 15.913 mmol). 1H NMR (DMSO-d6) δ ppm 7.81 (dd, J=8.3, 0.8 Hz, 1H), 7.23 (t, J=1.9 Hz, 1H), 6.99 (dt, J=8.3, 1.9 Hz, 1H), 5.75 (br s, 3H), 3.89 (s, 5H), 3.10 (d, J=22.0 Hz, 2H). MS (ES+): m/z 248.02 (100) [MH+]. HPLC: tR=1.68 min (ZQ3, polar—5 min).

Provenance & Evidence