Dimethyl Sulfoxide → 2-[(3,4-Dimethylphenyl)oxy]acetaldehyde

Participants

Reaction Conditions

Reaction Steps

A cooled (−78° C.) solution of oxalyl chloride (0.76 ml; 9.000 mmol) in anhydrous DCM (40 ml) was treated dropwise with a solution of dimethyl sulfoxide (1.40 ml; 18.000 mmol) in anhydrous DCM (6 ml). After 10 min., a solution of 2-(3,4-dimethyl-phenoxy)-ethanol (0.997 g; 6.000 mmol) in DCM (12 ml) was added dropwise, and the reaction mixture was further stirred at −78° C. for 30 min. TEA (4.17 ml; 30.000 mmol) was then added dropwise, and after 10 min. the resulting mixture was allowed to warm-up to 0° C. before a mixture of water (4 ml) and DCM (40 ml) was added. The aq. layer was extracted with DCM (2×40 ml), and the mixed organic layers were then washed with aq. sat. NaHCO3 (30 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure to give (3,4-dimethyl-phenoxy)-acetaldehyde as a yellow oil (0.985 g; 99%).

Provenance & Evidence