Dimethyl Sulfoxide → 2-Heptyloxy-4-iodobenzaldehyde

Participants

Reaction Steps

A solution of dimethyl sulfoxide (DMSO) (41.4 mmol, 3 ml) in dichloromethane (10 ml) is added to a solution of 1.8 ml of oxalyl chloride (20.7 mmol) in 55 ml of dichloromethane, dropwise, at −78° C. After stirring for 15 minutes, a solution of (2-heptyloxy-4-iodophenyl)methanol obtained in Step b (6.55 g, 18.8 mmol) in 25 ml of dichloromethane is added dropwise. After stirring for 20 minutes, 14 ml of triethylamine are added. After stirring for 2 hours, the reaction medium is hydrolysed by addition of water. The desired product is extracted by addition of ethyl acetate. The organic phase is washed with water, dried with magnesium sulfate and concentrated using a rotary evaporator. After evaporation of the solvents, 6.49 g (100%) of the expected compound are recovered in the form of a yellow solid.

Provenance & Evidence