Chromanone → Chroman-4-one oxime

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,3-dihydro-4H-chromen-4-one (3.00 g) in ethanol (15 ml)/water (3 ml) was added sodium acetate (6.64 g) and hydroxyl amine hydrochloride (5.52 g). The reaction mixture was heated at 70° C. for 1 h, poured into saturated sodium bicarbonate (50 ml), extracted methylene chloride (3×50 ml), dried MgSO4, filtered and concentrated to provide the title compound as a solid (3.22 g, 99%): 1H NMR (300 MHz, CDCl3) δ) 7.86, 7.28, 7.00-6.91, 4.27, 3.02; HRMS (FAB) calcd for C9H9NO2+H 164.0712, found 164.0703. Anal. Calcd for C9H9NO2: C, 66.25; H, 5.56; N, 8.58. Found: C, 66.21; H, 5.58; N, 8.57.

Provenance & Evidence