Reaction #531868

Reaction equation

trans-2-(4-Hydroxy-cyclohexyl)-isoindole-1,3-dione

triphenylphosphine

4-nitrobenzoic acid

diisopropyl azodicarboxylate

→

trans-4-Nitro-benzoic acid 4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-cyclohexyl ester

Solvents

THF

Conditions

Workup

1. 1
   OtherThe solvent was evaporated
2. 2
   Otherthe resulting solid was recrystallized from methanol

Procedure

To a solution of trans-2-(4-Hydroxy-cyclohexyl)-isoindole-1,3-dione (38 g, 154.9 mmol), triphenylphosphine (65 g, 248 mmol), and 4-nitrobenzoic acid (41.4 g, 248 mmol) in 1500 mL of THF was added dropwise diisopropyl azodicarboxylate (50.1 g, 248 mmol) at room temperature. The reaction mixture was stirred overnight. The solvent was evaporated, and the resulting solid was recrystallized from methanol. Yield: 53 g (86.7% of theory). 1H NMR (300 MHz, CDCl3): δ 8.40-8.36 (m, 4H), 7.79 (ddd, J=0.12, 0.02, and 0.02 Hz, 4H), 5.39 (s, 1H), 4.37-4.22 (m, 1H), 2.82-2.65 (m, 2H), 2.27-2.16 (m, 2H), 1.84-1.65 (m, 4H).

Source