Methane → Dodecyl 2-hydroxy-4-(methylthio)butanoate

Participants

Reaction Steps

To a 4 neck 1 L round bottom flask fitted with a reflux condenser, dean stark trap, thermocouple, and mechanical overhead stirrer was added 2-hydroxy-4-(methylthio)butanoic acid (150 g, 999 mmol, obtained for example by stirring Alimet over activated charcoal, filtering and concentrating in a rotovap), 1-dodecanol (335 mL, 1498 mmol), sodium hydrogen sulfate (2.40 g, 19.97 mmol) and toluene (625 mL). The reaction was heated to reflux with removal of water (19 mL) during the course of about 5.5 hours and the reaction was monitored by GC analysis. The reaction was cooled to room temperature overnight and then the organic layer was washed with saturated NaHCO3 (1×300 mL) and a white solid formed which was filtered. The organic layer was washed with water (1×300 mL) and brine (2×300 mL), dried over sodium sulfate, filtered and evaporated to give an amber oil (487 g). The oil was purified by kugelrohr distillation at 135° C. and 0.1 Torr vacuum to give an oil (133.18 g, 42%). m/z 341 (MNa+).

Provenance & Evidence