Acetic Acid → HCID 18399674, compound

Participants

Reaction Conditions

Reaction Steps

3,4-Methylenedioxy-bromobenzene (5 g, 23 mmol) was slowly added to a stirred solution of 35ml concentrated nitric acid and 105 ml glacial acetic acid maintained at 10° C. The reaction mixture was stirred at 15° C. for 1 h and then diluted with 200 ml ice cold water. The resulting mixture was extracted twice with 200 ml portions of ether. The combined organic phase was dried and evaporated in vacuo to give the crude product. The crude product was recrystallized from ethanol to give bright yellow needle shaped crystals of the nitro compound in 90% yield; mp 87-89° C.; IR(KBr) 1528, 1333; 1H NMR (CDCl3) δ6.14(2H,s), 7.12(1H, s), 7.45(1H, s); 13C NMR(CDCl3) δ104.0, 107.0, 109.0,114.3, 146.2, 148.0, 152.1; HRMS calcd for C3H4BrNO4: 244.9323; found: 244.9324.

Provenance & Evidence