3-Cyclopentoxy-4-nitrobenzyl alcohol → Benzaldehyde, 3-(cyclopentyloxy)-4-nitro-
Reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=2[N+:15]([O-:17])=[O:16])[CH2:10][OH:11])[CH2:5][CH2:4][CH2:3][CH2:2]1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=2[N+:15]([O-:17])=[O:16])[CH:10]=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirred solution of 5.0 g (21.1 mmol) of 3-cyclopentoxy-4-nitrobenzyl alcohol in 200 mL of dry methylene chloride is added 19.0 g (218.5 mmol) of activated manganese dioxide in one portion. The brown suspension is warmed to reflux for 48 hours after which time the mixture is cooled to room temperature, filtered over Celite 545 and concentrated. Liquid chromatography over 200 g of silica gel eluting with 30% ethyl acetate in hexane provided the desired, analytically pure compound upon drying in vacuo.