Dimethylformamide → HCID 58858094, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of the potassium salt of 4-nitroguaiacol (2.00 g, 9.65 mmol) and chloroacetone (1.15 mL, 14.5 mmol) in 20 mL of DMF was heated at 80° C. for 3 h. The suspension was cooled to rt and diluted with water. A precipitate formed which was filtered, washed with water and dried under vacuum to afford the title compound (1.63 g) as an off-white solid. 1H NMR (CDCl3) δ 2.29 (s, 3H), 3.96 (s, 3H), 4.71 (s, 2H), 6.74 (d, J=8.80 Hz, 1H), 7.76 (d, J=2.20 Hz, 1H), 7.84 (dd, J=8.79 Hz, 2.20 Hz, 1H); 13C NMR (CDCl3) δ 26.37, 56.33, 73.62, 107.11, 111.88, 117.36, 142.33, 149.23, 152.49, 203.40; HPLC (Method #1): 1.98 min, (100%); LCMS (ES): m/z 226 [M+H]+.

Provenance & Evidence