Benzaldehyde → 6329-46-0

Participants

Reaction Steps

Dimethyl phosphite (1.86 mL, 20.3 mmol, 1.03 eq) was added to benzaldehyde (2 mL, 19.8 mmol, 1 eq) and stirred for 5 min. KF (5.75 g, 99.0 mmol, 5 eq) was then added and the reaction mixture was stirred until it solidified (˜20 min). The crude product was then dissolved in DCM, filtered, and the solvent evaporated yielding 4 as a white powder (4.38 g, 100%). The product was dried under high vacuum over P2O5. No further purification was required. 1H NMR (400 MHz CDCl3) δ 7.53-7.45 (m, 2H), 7.43-7.23 (m, 3H), 5.05 (d, J=11.1 Hz, 1H), 3.67 (dd, J=14.3, 10.4 Hz, 6H). 13C NMR (101 MHz, CDCl3) δ 136.66 (s), 128.64 (s), 128.49 (s), 127.28 (d, JC-P=5.7 Hz), 70.86 (d, JC-P=159.6 Hz), 54.02 (dd, JC-P=28.4, 7.0 Hz). 31P NMR (162 MHz CDCl3) δ 24.71 (s). ESIMS calculated for C9H13O4PNa [M+Na]+239.06, found: 239.04; mp 85-86° C.

Provenance & Evidence