m-Chloroperbenzoic acid → HCID 23150273, compound
Reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.ClC1C=CC=C(C(OO)=[O:26])C=1>C(Cl)(Cl)Cl>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][N+:15]([O-:26])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 4-[4-(3-chloropropoxy)phenyl]pyridine (1.22 g) and metachloroperbenzoic acid (1.82 g) in chloroform (25 mL) is stirred at room temperature for four hours, then concentrated under reduced pressure and purified by column chromatography over silica gel using a gradient dichloromethane/methanol from 100/0 to 95/5. Fractions containing the expected product are pooled and concentrated under reduced pressure to give 1.09 g of 4-[4-(3-chloropropoxy)phenyl]pyridine 1-oxide as a pale yellow solid used without further purification.