2,3-Dimethyl-6-nitrobenzenemethanol → 2,3-Dimethyl-6-nitrobenzaldehyde

反応式

[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[CH2:12][OH:13].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl.C(OCC)C>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[CH:12]=[O:13]

参加物

実験手順

A solution of 2,3-dimethyl-6-nitrobenzenemethanol (34.88 g, 0.192 mole) in dichloromethane (150 mL) was added to a stirred mixture of pyridinium chlorochromate (62.2 g, 0.288 mole) in dichloromethane (250 ml). The mixture was stirred vigorously for 4 hours, diluted with diethyl ether (500 mL) and the organic layer decanted. The residue was washed with diethyl ether (500 mL) and the combined organic solution filtered through a plug of silica gel (6"×11/2"). Evaporation of the solvent afforded 2,3-dimethyl-6-nitrobenzaldehyde (32.08 g, 93%). An analytical sample was prepared by crystallizing from diisopropyl ether and had m.p. 66°-68° C.