Methyl Thioglycolate → HCID 9928750, compound

Participants

Reaction Steps

A slurry of ρ-toluenesulfonic acid monohydrate (1.50 g, 7.89 mmol) and activated 3 Å molecular sieves (300-500 mg) in 7 mL of toluene is stirred for 15 minutes. Methyl thioglycolate (410 mg, 3.86 mmol) is then added followed by 4,4'-bis(dimethyamino)benzhydrol (Aldrich) (950 mg, 3.51 mmol) and stirred for 1 hour. The reaction is diluted with ethyl acetate, washed with saturated aqueous sodium bicarbonate, brine and dried over magnesium sulfate. Chromatography on silica gel, eluting with a 1:4 mixture of ethyl acetate: hexane, provides methyl [[bis-(4-dimethylaminophenyl)methyl]thio]acetate as a greenish yellow solid in 53% yield.

Provenance & Evidence