Dimethyl Sulfoxide → Benzenepentanal

Participants

Reaction Conditions

Reaction Steps

To a solution of 15.9 mL (182.65 mmol, 1.2 eq) of oxalyl chloride in 300 mL of CH2Cl2 at -78° C. under argon is added dropwise 25.9 mL (365.3 mmol, 2.4 eq) of DMSO in 40 mL of CH2Cl2. After stirring for 1 hour at -78° C., 25 g (152.21 mmol) of 5-phenyl-1-pentanol dissolved in 40 mL of CH2Cl2 is added dropwise. After stirring for 2 hour at -78° C., 106 mL (761.03 mmol, 5 eq) of triethylamine is added dropwise. This then stirred at -78° C. for 1 hours then at 25° C. for overnight. The reaction is partitioned between CH2Cl2 and 1 N HCl. The organic layer is washed well with water, dried over anhydrous MgSO4 and concentrated in vacuo to afford 23.52 g (95%) of 5-phenylpentanal in the form of a yellow oil.

Provenance & Evidence