Benzaldehyde, 2-(trifluoromethoxy)-, oxime, [C(E)]- synthesis

Yield:1383740-00-8 93%

Reaction Conditions:

with hydroxyamino hydrochloride;sodium hydroxide in ethanol;lithium hydroxide monohydrate at 0 - 20; for 1 h;

Steps:

4.1.1. (E)-2-(trifluoromethoxy)benzaldehyde oxime (2)

A solution of NH2OHHCl (2.2 g, 31.7 mmol) in water (20 mL)was added to a solution of sodium hydroxide (1.2 g, 30 mmol) inwater (20 mL) at 0 C. The resulting solution was stirred for at 0 C,to which was then added a solution of 2-(trifluoromethoxy)-benzaldehyde 1 (5.0 g, 26.3 mmol) in ethanol (20 mL). The reactionwas stirred at rt for 1 h. After completion, the reaction solutionwasdiluted with water and extracted with ethyl acetate. The organiclayers were combined, washed with brine, dried over anhydroussodium sulfate, and concentrated under vacuum to give 5.0 g ofcompound 2 in 93% yield used directly in the next step, MS (ESI) m/z: 206.1 [MH].

References:

Luo, Guoshun;Lin, Xin;Li, Zhenbang;Xiao, Maoxu;Li, Xinyu;Zhang, Dayong;Xiang, Hua [European Journal of Medicinal Chemistry,2021,vol. 209,art. no. 112910]