Synthesis of N-phenyloxyphthalimide
A different 25 mL round bottom flask was taken out of an oven and stoppered. 2 mL of DMF was added to the new flask. Then 61.7 mg of t-BuOK and 81.6 mg of N-hydroxyphthalimide were added. The mixture then turned a dark red color. It was then stirred for 10 minutes. It then turned a bright orange color. Then 2 mL more of DMF was added. It was then stirred until it became a liquid. Then the Diaryliodonium Triflate Salt which was produced in the last step, was added. It turned a light yellow color. It was then stirred for 1 hour.
The solution was then poured into a separatory funnel. 20 mL of deionized (DI) water and 20 mL of ethyl acetate was added to the separatory funnel. The bottom aqueous layer was then drained. DI water was added and the bottom layer was drained again. This step was done again, but the solution this time looked like milk. Then, 20 mL of DI water and 20 mL of brine was added. The bottom layer was then drained and the solution was put in an erlenmeyer flask. The solution was cloudy and white.
To this flask, anhydrous sulfate was added to remove water. The solution then started to settle and become clear. It was then gravity filtered, and the solution was put into a dry round bottom flask. This was then concentrated using a rotary evaporator. The compound was 110 mg.
The solution was then poured into a separatory funnel. 20 mL of deionized (DI) water and 20 mL of ethyl acetate was added to the separatory funnel. The bottom aqueous layer was then drained. DI water was added and the bottom layer was drained again. This step was done again, but the solution this time looked like milk. Then, 20 mL of DI water and 20 mL of brine was added. The bottom layer was then drained and the solution was put in an erlenmeyer flask. The solution was cloudy and white.
To this flask, anhydrous sulfate was added to remove water. The solution then started to settle and become clear. It was then gravity filtered, and the solution was put into a dry round bottom flask. This was then concentrated using a rotary evaporator. The compound was 110 mg.