Sodium Hydroxide → O-(Diphenylphosphinyl)hydroxylamine

Participants

Reaction Steps

To hydroxylamine hydrochloride (15.86 g, 228.2 mmol) in water (35 mL) cooled in an ice-salt bath was added 7.1 N aqueous sodium hydroxide (27.4 mL, 194.4 mmol) followed by 1,4-dioxane (100 mL). The solution was vigorously stirred for 15 min and then chlorodiphenylphosphine oxide (20.00 g, 84.52 mmol) was added as a solution in 1,4-dioxane (100 mL). The solution was stirred an additional 15 min as a white precipitate formed. The precipitate was collected and then suspended in cold (0°) 0.25 N aqueous sodium hydroxide (250 mL). The mixture was stirred for 1 h and then the solid was collected, washed with water (100 mL), and thoroughly dried under vacuum to afford the desired intermediate (7.09 g, 36%) as a white solid. 1H-NMR (300 MHz, DMSO-d6) 7.65-7.74 (m, 4H), 7.38-7.42 (m, 6H); 31P-NMR (DMSO-d6) 23.11 (br s, 1P).

Provenance & Evidence