1-Dodecanethiol → HCID 59590777, compound

Temperature

125 °C

A screw-cap vial was charged with 42.2 (0.195 g, 0.832 mmol), NMP (0.8 mL), sodium hydroxide (0.150 g, 3.75 mmol), and 1-dodecanethiol (available from Aldrich) (0.699 mL, 2.91 mmol). The mixture was stirred overnight at 125° C. (sealed vial) and cooled to room temperature. Additional NMP (0.8 mL), sodium hydroxide (0.150 g, 3.75 mmol), and 1-dodecanethiol (0.699 mL, 2.91 mmol) were added, and the mixture was stirred for 72 hours at 125° C. and cooled to room temperature. The solidified mixture was fractured with a spatula, diluted with 1 N HCl, and extracted with EtOAc. The combined organic layers were washed with water and brine, dried (MgSO4), and concentrated. The residue was purified by silica gel flash chromatography (20-50% EtOAc/hexanes) to afford 42.3 (0.119 g, 65% yield) as a brown oil.

1. custom(sealed vial)
2. temperaturecooled to room temperature
3. stirringthe mixture was stirred for 72 hours at 125° C.
4. temperaturecooled to room temperature
5. extractionextracted with EtOAc
6. washThe combined organic layers were washed with water and brine
7. dry with materialdried (MgSO4)
8. concentrationconcentrated
9. customThe residue was purified by silica gel flash chromatography (20-50% EtOAc/hexanes)

ORD record

ord-02784f66988e4d85818d9dc473503a39

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08450522B2