end of this addition the temperature of the reaction mixture was 18 u00b0 c after stirring an additional 3 minutes the methylene chloride layer was separated and analyzed by gas chromatography this layer was found to contain t butyl isocyanate in the amount equal to 83 of the theoretical yield with rapid stirring 2 ethylhexanoyl chloride 50 g 307 mmol was added dropwise over 20 minutes to excess ammonium hydroxide 250 ml that had been cooled to 0 u00b0 in an ice bath the bath was then removed and stirring continued for 90 minutes the white solid product was recovered by filtration washed three times with 50 ml portions of water and dried at 50 u00b0 in a vacuum oven to give 36 g 82 of the desired amide m p 105 u00b0 lit m p 101 u00b0 102 u00b0 2 ethylhexyl carboxamide 35 75 g 250 mmol was suspended in 300 ml of ethyl acetate and cooled to 1 u00b0 hypochlorous acid 43 3 g of 30 6 solution 252 m mol was added dropwise over 13 minutes with stirring after 10 minutes the cooling bath was removed and stirring continued for 1 hour while the mixture warmed to room temperature the ethyl acetate layer was then separated and dried mgso 4 and the solvent was removed on the rotary evaporator and finally on the vacuum pump to give 44 g 98 of colorless liquid n chloro 2 ethylhexyl carboxamide n chloro 2 ethylhexyl carboxamide 44 g 250 m mol methylene chloride 200 ml and 5 mole percent based on the amide of tetrabutyl ammonium bisulphate phase transfer catalyst were stirred and cooled to 1 u00b0 in an ice bath a solution of sodium hydroxide 9.