Sodium Hydroxide → HCID 797883, compound

Participants

Reaction Steps

4-(3-Fluoro-benzyloxy)-benzaldehyde (which may be prepared as described in Brabanti, E. et al. WO 2007147491 or may be purchased from Matrix Scientific, Columbia, S.C. 29224-5067; 24 g, 78.2 mmol) was taken up in 9:1 EtOH/H2O (200 mL) and hydroxylamine hydrochloride (8.15 g, 117.3 mmol) was added. A solution of NaOH (7.51 g, 187.6 mmol) in 9:1 EtOH/H2O was added dropwise by addition funnel over 30 min. The mixture was heated at reflux for 4 h, then allowed to cool and acidified to pH 5 by adding glacial AcOH (17 mL). The solid was filtered off and dissolved in EtOAc. The organic solution was dried over Na2SO4, filtered, and evaporated to give 4-(3-fluoro-benzyloxy)-benzaldehyde oxime (6.6 g, 25%).

Provenance & Evidence