Dimethyl Sulfoxide → 4-Pentenoic acid

Participants

Reaction Conditions

Reaction Steps

A 500 mL three-necked round-bottom flask equipped with magnetic stirring, oil bath heat, and connection to a nitrogen bubbler was charged with 17.2 g of N-methylperfluorobutanesulfonamide (C4F9SO2NHCH3) and 250 mL dimethyl sulfoxide. Stirring was begun, and the solid dissolved within a few minutes. A solution of 4.0 g of potassium hydroxide in 5 mL of water was added via pipette, and stirring was continued for another 30 min while the oil bath was heated to 80° C. By the end of this period most of the potassium hydroxide had dissolved. 11-Bromo-1-undecene, obtained from Aldrich Chemical Co. (95 percent purity, 12.3 g) was then added to the flask via pipette, and the reaction mixture was left to stir for 19 hr at 80° C. The oil bath was then removed to allow the mixture to cool, and the flask contents were poured into a separatory funnel. The mixture separated into two liquid phases, and the lower layer was drawn off. The upper phase was diluted with an equal volume of water, causing separation of a small amount of lower phase. This was also drawn off and combined with the first batch. The combined crude product (18.0 g) was dissolved in 150 ml dichloromethane and washed successively with 100 ml portions of water, 10 weight percent aqueous potassium hydroxide solution, water, and brine. The dichloromethane solution was dried over anhydrous magnesium sulfate and filtered, then solvent was removed on a rotary evaporator at water aspirator pressure. This left 17.9 g light straw-colored liquid product. Bulb-to-bulb vacuum distillation of 17.3 g crude product at 160-180° C. and 0.3 torr (4 Pa) gave 16.2 g of N-(10-undecenyl)-N-methylperfluorobutanesulfonamide as a clear, colorless liquid distillate.

Provenance & Evidence