Formaldehyde → N-(Hydroxymethyl)phenylacetamide

Participants

Reaction Steps

A mixture of phenylacetamide 12 (2 g, 15 mmol) in a solution of potassium carbonate (4%, 2 ml, 0.6 mmol) and an aqueous solution of formaldehyde (37%, 2 ml, 20 mmol) was refluxed for 15 min (until completely dissolved). The mixture was cooled and extracted with CH2Cl2 (2×30 ml). The combined organic phases were dried over MgSO4 and were concentrated under reduced pressure to give a crude product (1.35 g), recrystallization in toluene (20 ml) gave N-hydroxymethylphenylacetamide 11 (1.1 g, 44%) in the form of a white powder. M.p. 78° C. 1H NMR (CDCl3, 300 MHz) δ 7.50-7.20 (m, 5H), 6.48 (br s, NH), 4.69 (t, J=7.0 Hz, 2H), 3.67 (t, J=7 Hz, OH), 3.60 (s, 2H). 13C NMR (CDCl3, 75 MHz) δ 172.9, 134.4, 129.5, 129.0, 127.5, 64.2, 43.6.

Provenance & Evidence