Methanol → Diethyl 3-(N-Hydroxyamino)propylphosphate

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Reaction Steps

Firstly 32.0 g (0.8 mol) of sodium hydroxide dissolved in 75 ml water then 75 ml methanol, and finally 25.5 g (0.098 mol) 3-bromopropyl phosphonic acid diethylester were added drop by drop to a solution of 55.6 g (0.8 mol) hydroxylamine hydrochloride in 100 ml water with cooling with ice. This led to a clouding of the solution. After 3 hours stirring at a temperature of 40 to 45° C. methanol was removed under reduced pressure, the resulting aqueous solution was saturated with NaHCO3 (pH=8), shaken out three times with 60 ml toluene in each case (the toluene phase was discarded) and then shaken out with chloroform (1× with 90 ml, 2× with 50 ml in each case). The slightly yellowy chloroform phase was dried over MgSO4. After filtering of the dehydrating agent the solution was concentrated under reduced pressure. 15.43 g (0.0728 mol) 3-(N-hydroxyamino)-propylphosphonic acid diethylester were obtained as an almost colourless oil. This corresponds to a yield of 74.3% (DE-A-27 33 658).

Provenance & Evidence