3-chloro-4-(2-methylpropyl)benzaldehyde

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of sodium chlorite (80% assay, 1.06 g, 0.0094 mol) and sodium dihydrogenphosphate dihydrate (3.33 g, 0.0213 mol) in demineralized water (10 mL) is added in two equal lots (one hr interval) to a solution of 3-chloro-4-isobutylbenzaldehyde (0.7 g, 0.0036 mol) in tert-butanol (10 mL) at room temperature. After completion of addition, stirring at room temperature is continued for 4 hrs. It is then extracted in ethyl acetate (2×30 mL). Combined organic layer is dried over sodium sulfate and concentrated under reduced pressure to give 3-chloro-4-isobutylbenzoic acid. After completion of addition It is then extracted in ethyl acetate (2×30 mL) Combined organic layer is dried over sodium sulfate concentrated under reduced pressure

Conditions: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. is slowly brought to 60-65° C. During cooling formation of solid to stir for 10 minutes at this temperature stirred for 20 minutes The reaction mixture is extracted in ethyl acetate (2×30 mL) Combined organic layer is dried over sodium sulfate concentrated to get the crude, which is purified