[CH2:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][C:6]=1[N+]([O-])=O)[CH:2]([CH3:4])[CH3:3].N([O-])=O.[Na+].[ClH:20]>O>[Cl:20][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:5]=1[CH2:1][CH:2]([CH3:4])[CH3:3])[CH:9]=[O:10]4-Isobutyl-3-nitrobenzaldehyde (3.3 g, 0.0159 mol) is added to a solution of stannous chloride (8.37 g, 0.0441 mol) in concentrated hydrochloric acid (23 mL) at 0-5° C. The reaction mixture is slowly brought to 60-65° C. and is stirred at this temperature for 30 minutes. The reaction mixture is again cooled to 0-5° C. During cooling formation of solid is observed which is broken before proceeding further. Solution of sodium nitrite (1.36 g, 0.0188 mol) in demineralized water (3 mL) is added to the above reaction mixture at 0-5° C., allowed to stir for 10 minutes at this temperature. It is then poured into a slurry of cuprous chloride (3.6 g, 0.0346 mol) in demineralized water (5 mL) at 60-65° C. & stirred for 20 minutes. The reaction mixture is extracted in ethyl acetate (2×30 mL). Combined organic layer is dried over sodium sulfate and concentrated to get the crude, which is purified using column chromatography (230-400 mesh; toluene:n-hexane, 3:7) to yield 3-chloro-4-isobutylbenzaldehyde.
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