Formaldehyde → N-[1-(hydroxymethyl)-2-oxo-2-phenylethyl]acetamide

Participants

Reaction Steps

N-(1-oxo-1-phenylethan-2-yl)acetamide (10) (1.1 g, 6.0 mmol, 1.0 equiv.) was added to a 100 mL RBF followed by EtOH (25 mL, 200 proof). Next, a 0.5 M solution of NaHCO3 (250 mg, 3.0 mmol, 0.5 equiv.) was added followed by a 37% solution of formaldehyde (730 μL, 9.0 mmol, 1.5 equiv.). The solution was stirred at rt. for 24 h and transferred to a separatory funnel with a 1.0 M solution of NaCl (2.9 g, 50.0 mmol). The solution was extracted with CH2Cl2 (5×60 mL). The organic layer was dried over Na2SO4, concentrated on a rotary evaporator, and dried under vacuum to give a crude off-white solid. The solid was washed with EtOAc (10 mL) to remove all impurities. The remaining solid was dried under vacuum to give 900 mg (72%) of 11 as a white solid. Rf=0.11 (5% MeOH/CH2Cl2); mp=115-117° C.; IR (KBr) 3312, 3262, 2915, 1696, 1639, 1537, 1228, 1101 cm−1; 1H NMR (500 MHz, CDCl3) δ 8.00 (d, J=7.0 Hz, 2H, Ph-H), 7.61 (t, J=7.0 Hz, 1H, Ph-H), 7.48 (t, J=7.0 Hz, 2H, Ph-H), 7.17 (d, J=7.0 Hz, 1H, Ac—NH), 5.63 (m, 1H, Ac—NH—CH), 4.01 (m, 1H, CH—CH2), 3.88 (m, 1H, CH—CH2), 2.06 (s, 3H, NH—COCH3); 13C NMR (125 MHz, CDCl3) δ 197.0, 171.2, 134.3, 129.1, 128.9, 64.4, 57.3, 23.2; LRMS (ESI-MS m/z): Mass calcd for C11H13NNaO3 [M+Na]+, 230.22. Found 208. Anal. calcd for C11H13NO3: C, 63.76; H, 6.32; N, 6.76. Found: C, 63.92; H, 6.34; N, 6.74. Spectroscopic data were consistent with the literature data for this compound.

Provenance & Evidence