CC1C=CC=C(C)C=1C(O)=O.[CH3:12][C:13]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[C:18]([CH3:25])[C:14]=1[C:15]([OH:17])=[O:16].CO>O1CCCC1>[CH3:12][C:13]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[C:18]([CH3:25])[C:14]=1[C:15]([OH:17])=[O:16].[CH3:12][C:13]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[C:18]([CH3:25])[C:14]=1[CH2:15][OH:16]
2,6-Dimethyl-3-nitrobenzoic acid was prepared by nitrating 2,6-dimethylbenzoic acid. A solution of 2,6-dimethyl-3-nitrobenzoic acid (30 grams, 0.15 mole) in tetrahydrofuran (100 ml) was stirred under nitrogen. Borane-methyl sulfide complex (20 ml, 0.2 mole) was added dropwise at room temperature. When one fourth of the borane complex had been added the reaction mixture was brought to reflux. Reflux continued for one hour after complete addition of the borane complex. The reaction mixture was cooled to 0°, and cold methanol (500 ml) was added dropwise until foaming ceased and then added rapidly. The solvent was evaporated, and the crude product was dissolved in methylene chloride and washed with 2 N sodium hydroxide. The solvent was removed by evaporation to give (2,6-dimethyl-3-nitrophenyl)methanol (12.0 grams; mp 84°-92°).
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