Dimethyl Sulfoxide → 2-(Tert-Butylthio)Benzaldehyde

Participants

Reaction Conditions

Reaction Steps

Powdered potassium hydroxide (21.9 g, 390 mmol) and 56 ml (497 mmol) of terbutyl mercaptan were mixed 55.5 ml of dimethylsulfoxide in a 250 ml three-neck flask. To this stirred mixture was added dropwise over a ten minute period 50 g (356 mmol) of 2-chloro-benzaldehyde. During addition of the 2-chlorobenzaldehyde, the reaction mixture warmed to 120° C. After addition was complete, the mixture was allowed to react at about 110° C. for 1.5 hours. At the end of this time, the mixture was cooled to room temperature and taken up on 600 ml of ethyl acetate and 1 liter of water. The organic layer was separated, dried and evaporated to yield 2-(1,1-dimethylethylthio)benzaldehyde, b.p. 80°-82° C. at 0.05 mm Hg, which was used without further purification in the next step of the process.

Provenance & Evidence