4-(2-chloroethyl)benzaldehyde

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-(2-Chloroethyl)benzaldehyde (1.70 g, 10.08 mmol) was dissolved in ethanol (35 ml), hydroxylamine hydrochloride (1.05 g, 15.11 mmol) was added, and the mixture was stirred at 50° C. for 2 hours. Ethanol was evaporated under reduced pressure, and water was added. The mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (1.75 g, 95%). Ethanol was evaporated under reduced pressure, and water was added The mixture was extracted with ethyl acetate The extract was washed with saturated brine dried over anhydrous sodium sulfate The solvent was evaporated under reduced pressure

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

Procedure: 4-(2-Chloroethyl)benzoic acid (2.00 g, 10.83 mmol) was dissolved in THF (40 ml) under an argon atmosphere, and 1M borane-THF complex (16 ml, 16.00 mmol) was slowly added dropwise under ice-cooling. After stirring at room temperature for 2 hours, 1N sulfuric acid (36 ml) was added, and the mixture was stirred for 1 hour and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained crude product was dissolved in dichloromethane (50 ml). Manganese dioxide (10.00 g) was added, and the mixture was stirred overnight at room temperature. After filtration through celite, the filtrate was concentrated under reduced pressure to give the title compound (1.71 g, 91%). 1M borane-THF complex (16 ml, 16.00 mmol) was slowly added dropwise under ice- cooling the mixture was stirred for 1 hour extracted with ethyl acetate The organic layer was washed with saturated brine dried over anhydrous sodium sulfate The solvent was evaporated under reduced pressure the obtained crude product the mixture was stirred overnight at room temperature After filtration through celite the filtrate was concentrated under reduced pressure