[OH-:1].[K+].O.Cl[C:5]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:6].[Cl-].O[NH3+:19]>CCOCC>[CH2:8]([O:7][C:5](=[O:6])[NH:19][OH:1])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]A solution of 112 parts of potassium hydroxide in 1000 parts of water and 206.5 parts of nonyl chloroformate were added at equivalent rates over 2 hours to a stirred suspension of 69.5 parts of ground hydroxyl ammonium chloride in 1000 parts of ether at 0° C. to 5° C. The reaction mixture was stirred for a further 3 hours at 0°-5° C. followed by 18 hours at 25° C. and was then filtered to remove potassium chloride. The ether layer was separated, washed with water, dried, filtered and evaporated to constant weight at 40° C. under reduced pressure to give 190 parts of nonyl-N-hydroxycarbamate as a colourless oil.
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