Phenylacetic Acid → Dimethyl phenylacetylphosphonate

Participants

Reaction Steps

This compound was prepared from phenylacetic acid (0.68 g, 5.0 mmol) as described for the preparation of the trimethylsilyl analogue 50a. The reaction furnished 1.17 g of 50b as a white solid, mp. 117-122° C. (hygroscopic). IR (film): 3600-2600, 1457, 1312, 1237 and 1053; 1H NMR (200 MHz, CDCl3): δ3.83 (6H, d, J=11 Hz), 6.07 (1H, d, J=12 Hz) and 7.52 (5H, m); 13C NMR (50 MHz, CDCl3): δ53.6, 116.3, 116.8, 127.2, 127.3, 127.9, 129.2, 133.7, 134.1, 137.8 and 141.9; 31P (202 MHz; CDCl3; H3PO4): δ16.1; HR-MS (EI): mi/e 228.0550 (M+C10H13O4P requires 228.0551).

Provenance & Evidence