4-Nitrobenzoic Acid → HCID 178525746, compound

Participants

Reaction Steps

To a solution of trans-2-(4-hydroxy-cyclohexyl)-isoindole-1,3-dione (38 g, 155 mmol), triphenylphosphine (65 g, 248 mmol), and 4-nitrobenzoic acid (41 g, 248 mmol) in 1500 mL of THF was added dropwise diisopropyl azodicarboxylate (50 g, 248 mmol) at room temperature. The reaction mixture was stirred overnight. The solvent was evaporated, and the resulting solid was recrystallized from methanol to afford 53 g (87%) of the title compound as a white solid. 1H NMR (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).

Provenance & Evidence