Acetone → HCID 51036371, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(trifluoromethyl)-4-hydroxybenzaldehyde (2.19 g, 12 mmol) in acetone (423 μL, 5.8 mmol) was dissolved in glacial acetic acid (9 mL), saturated with anhydrous HCl and heated to 25-30° C. for 2 h. The red solution was stirred for 36 h and treated with cold water. The reaction mixture turned into a dark green suspension and the resulting precipitate was filtered, washed with water and dried in vacuo to afford NW310.1 as a dark green solid (740 mg, 32%). mp: 233-234° C. 1H NMR (250 MHz, CD3OD) δ (ppm): 7.86 (d, 4J=1.6 Hz, 2H, HAr), 7.80 (d, 3J=8.8 Hz, 4J=1.9 Hz, 2H, HAr), 7.75 (d, 3J=16.1 Hz, 2H, Hvin), 7.15 (d, 3, J=15.9 Hz, 2H, Hvin), 7.02 (d, 3J=8.6 Hz, 2H, HAr). 13C NMR (75 MHz, CD3OD) δ (ppm): 191.6 (C), 159.9 (C), 144.3 (CH), 134.8 (CH), 129.3 (CH), 127.8 (C), 127.3 (C), 125.3 (CH), 118.8 (CH). MS (FAB) m/z: 403.2 (M+). Anal. calcd for C19H12F6O3. 1H2O: C, 54.17; H, 3.59. Found: C, 54.39; H, 3.31%.

Provenance & Evidence