To a solution of 5.75 gm (0.0825 mole) of hydroxylamine hydrochloride in 25 ml of dimethylsulfoxide (DMSO) and 1.0 ml of water in a 3-necked round bottom flask equipped with a mechanical stirrer, a thermometer, and a condenser is added 22.7 gm (0.27 mole) of sodium bicarbonate. The mixture is stirred and a stream of nitrogen kept throughout the reaction. To this solution is added 33.8 gm (0.182 mole) of 2-methoxyethyl iodide and the stirring continued at 35°C for 20 hr. The temperature is then increased to 50°C, and kept at this temperature for 4 hr. The mixture is made pH 8 by means of 50% sodium hydroxide and extracted several times with 100-ml portions of toluene (original procedure uses benzene), then filtered, and the solids are washed again with toluene. The extracts are dried and concentrated to give 37.0 gm of an oil, which contains (as determined by gas chromatography) 23.0% of bis(3-methoxyethyl)hy-droxylamine (62.7% overall yield) and 9.0% of 2-methoxyethylamine (20.1% yield).
