p-(Trifluoromethoxy)benzaldehyde → 4-(trifluoromethoxy)benzaldehyde oxime

Temperature

65 °C

A mixture of 4-(trifluoromethoxy)benzaldehyde (9.5 g, 50 mmol) and hydroxylamine hydrochloride (5.3 g, 75 mmol) in methanol (80 mL) was heated at 65° C. for 2 h. The volatiles were removed under reduced pressure and the residue was dissolved in EtOAc, and washed with H2O, brine. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The solid thus obtained was then recrystallized from EtOAc and petroleum ether to afford the title compound (9.5 g, 93%) as an off-white solid. 1H NMR (500 MHz, CDCl3) δ 8.08 (s, 1H), 7.52 (d, J=7.2 Hz, 2H), 7.15 (d, J=6.8 Hz, 2H).

1. customThe volatiles were removed under reduced pressure
2. dissolutionthe residue was dissolved in EtOAc
3. washwashed with H2O, brine
4. dry with materialThe organic layer was dried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe solid thus obtained
8. customwas then recrystallized from EtOAc and petroleum ether

ORD record

ord-f6438604172d475fb5707ac7656662ab

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09018380B2