Ceric ammonium nitrate → HCID 18932707, compound
Reaction equation
[CH2:1]([CH:3]1[CH2:12][C:11]2[C:6](=[C:7]([O:15]C)[CH:8]=[CH:9][C:10]=2[O:13]C)[CH2:5][O:4]1)[CH3:2].O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+]>C(#N)C>[O:13]=[C:10]1[CH:9]=[CH:8][C:7](=[O:15])[C:6]2[CH2:5][O:4][CH:3]([CH2:1][CH3:2])[CH2:12][C:11]1=2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3-ethyl-5,8-dimethoxy-isochroman (300 mg; 1.35 mmol) in acetonitrile (10 ml) at room temperature was added dropwise a solution of CAN (prepared by dissolving ceric ammonium nitrate (2.22 g; 4.0 mmol) in water (5 ml)). The resulting mixture was quenched with saturated bicarbonate solution and extracted with dichloromethane. The combined organic layers were washed with brine and dried over Na2SO4 affording the crude title compound (251 mg; 97%) which was used as such for subsequent steps.