Hydrolysis of N-phenyloxyphthalimide
110 mg of our compound would be put into a 100 mL round bottom flask. 15 mL of glacial acetic acid (AcOH) and 5 mL of 37% HCl would be added to the round bottom flask. The flask would be put into a standard reflux set-up with a variac (120v@50) and a mantle. 1 mL of 37% HCl would be added periodically to the solution as it refluxed. Heating would be stopped after 2 hours. The solution would be cooled to room temperature. The solution would be then concentrated rotary evaporated to remove the acid. The compound would be then scraped into a 50 mL E flask. The reaction round bottom flask rinsed with DI and the rinses were poured into the erlenmeyer flask. The total volume of the rinses shouldn’t have gone over 20 mL. The solution would be then made alkaline using sodium hydroxide. The solution would be then transferred to a 125 mL separatory funnel and then it would be rinsed 3 times using CH2Cl2(30 mL) and put into the separatory funnel. The combined organic phases were dried over anhydrous sodium sulfate. This would be then gravity filtered. HCl would be bubbled in the solution until there would be no precipitate left. The solution would be stirred for 30 mins. The solution would be suction filtered. The solid would be set aside to dry overnight.