Dimethyl Sulfoxide → Benzenepentanal

Participants

Reaction Conditions

Reaction Steps

To a mechanically stirred solution of oxalyl chloride (21.6 g; 170 mmol) in dry CH2Cl2 (400 mL) at -78° C. is added DMSO (22.3 g; 360 mmol) dropwise over 45 minutes. After stirring 15 minutes 5-phenylpentanol (25 g; 150 mmol) is added and the internal temperature is allowed to warm to -55° C. After stirring at this temperature for 30 minutes the reaction is cooled to -78° C. and triethylamine (104 mL; 750 mmol) is added slowly over 20 minutes. After stirring 15 minutes the reaction bath is removed and the temperature is allowed to warm to 20° C. over 40 minutes. The reaction mixture is then washed with 500 mL water. The water layer is then back-extracted with CH2Cl2 (2×50 mL). The combined organic fractions are washed with 300 mL 2 N HCl, 100 mL water, 200 mL NaHCO3, 100 mL brine and dried (MgSO4). The solution is concentrated in vacuo to obtain 5-phenylpentanal (25 g) which is used directly in Step B.

Provenance & Evidence