4-phenylbutanal

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

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

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

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

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

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

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

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

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

Procedure: To a solution of 4-phenylbutanol (1 g) in dichloromethane (35 mL) at 0° C. was added PDC (7.5 g). The resulting suspension was stirred for 2 h at room temperature. The reaction solution was then filtered through a pad of silica gel. Concentration of the filtrate and flash chromatography of the residue (20% ethyl acetate/hexanes) provided 4-phenylbutanal (237 mg) as a colorless oil. The reaction solution was then filtered through a pad of silica gel

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

Procedure: To a stirred suspension of 4-phenylbutyronitrile (21.7 g, 0.12 mole) in ether (400 ml) at 78° C. is added 85 ml. of 25.3% diisobutylaluminum hydride in toluene over a period of 1 hour. After an additional 1 hour, the dry ice-acetone bath is removed and the reaction mixture is stirred at ambient temperature for 3 hours. The reaction mixture is added slowly to 5% aqueous sulfuric acid and then is extracted with several portions of ether. The ether extracts are combined, washed with water and saturated aqueous sodium chloride solution and dried over magnesium sulfate. After removal of the ether, the residual yellow oil is distilled in vacuo to give an oil. is added 85 ml the dry ice-acetone bath is removed The reaction mixture is added slowly to 5% aqueous sulfuric acid is extracted with several portions of ether washed with water and saturated aqueous sodium chloride solution dried over magnesium sulfate After removal of the ether the residual yellow oil is distilled in vacuo to give an oil

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

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