[CH3:1][CH:2]([CH3:7])[CH2:3][C:4](=[O:6])[CH3:5].O.[N+:9]([CH:12]([CH:15]=O)[CH:13]=O)([O-:11])=[O:10].[Na].[OH-].[Na+]>C(O)C.O>[CH:2]([C:3]1[CH:15]=[C:12]([N+:9]([O-:11])=[O:10])[CH:13]=[CH:5][C:4]=1[OH:6])([CH3:7])[CH3:1]4-Methyl-2-pentanone (4.85 g, 48 mmol) in 40 mL of ethanol was added dropwise to a solution of sodium nitromalonaldehyde monohydrate (7.61 g, 48 mmol) in 40 mL of water. NaOH (48 ml of 1N aqueous solution) was then added to the reaction mixture. The mixture was stirred at room temperature overnight, and solvent was removed under reduced pressure. The residue was diluted with water and neutralized, then extracted with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography with silica eluting with 15% ethyl acetate in hexanes to yield 4.7 g of 2-isopropyl-4-nitrophenol.
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