Hydroxyamine hydrochloride → (p-Chlorophenyl)-1,1,1-trifluoro-2-propanone oxime

Participants

Reaction Steps

A solution of 3-(p-chlorophenyl)-1,1,1-trifluoro-2-propanone (10.0 g, 0.045 mol) in ethanol (60 mL) is treated with a solution of hydroxylamine hydrochloride (4.68 g, 0.067 mol) in water (20 mL) and then with a solution of sodium acetate (5.53 g, 0.067 mol) in water (20 mL). The reaction mixture is refluxed for 2 hours, cooled, diluted with water, and extracted with ether. The combined ether extracts are washed sequentially with water and brine, dried (Na2SO4) and evaporated to a liquid which solidifies upon standing to give the title compound as white needles (11.84 g): IR (neat) 3300 cm-1 (broad); 1H NMR (CDCl3) δ3.86 (s, 2H, CH2), 7.23 and 7.30 (AB,JAB =8.6 Hz, ArH), 19F NMR δ-69.2; 13C NMR δ29.3 (s, CH2), 120.8 (q, 1JCF =274.5 Hz, CF3), 128.8, 130.3, 132.5, 133.1 (Aromatic C), 148.4 (q 2JCF =32.1 Hz, CO).

Provenance & Evidence