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

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 (125 g, 832.2 mmol, obtained for example by stirring Alimet over activated charcoal, filtering and concentrating in a rotovap), 1-decanol (238 mL, 1248 mmol), sodium hydrogen sulfate (1.998 g, 16.64 mmol), and toluene (625 mL). The reaction was heated to reflux with removal of water (16 mL) during the course of about 6 hours and the reaction was monitored by GC analysis. The reaction was cooled to room temperature overnight and the organic layer was washed with saturated NaHCO3 (1×300 mL), DI water (1×300 mL) and brine (2×300 mL), dried over sodium sulfate, filtered and evaporated to give an amber oil (395.5 g). The oil was purified by kugelrohr distillation at 110° C. and 0.1 Torr vacuum to give an oil (105.23 g, 43.5%). m/z 313 (MNa+);

1. customTo a 4 neck 1 L round bottom flask fitted with a reflux condenser, dean stark trap
2. filtrationfiltering
3. temperatureThe reaction was heated
4. washthe organic layer was washed with saturated NaHCO3 (1×300 mL), DI water (1×300 mL) and brine (2×300 mL)
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. customevaporated

ORD record

ord-0a6b743a53924e59a801996449794828

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09169203B2