tert-Butyl mercaptan → Di-tert-butyl sulphide

Temperature

0 °C

To a 50 mL round bottom flask containing 0.9 grams (8.82 mmole) of the sodium salt of 2-methyl-2-propanethiol was added 0.25 grams of sodium hydride (11.3 mmole) and the resulting mixture placed under vacuum and then under a nitrogen atmosphere. To the mixture was then added 15 mL of anhydrous tetrahydrofuran and the mixture cooled to 0° C. To the cooled mixture was added 1.5 grams (5.84 mmole) of 9 dissolved in 15 mL of anhydrous THF over a period of 10 minutes. After addition, the reaction mixture was allowed to stir, at room temperature and under a nitrogen atmosphere for 18 hours. After 18 hours the volatile components of the reaction mixture were removed under reduced pressure to give a brown solid. The brown solid was dissolved in 80 mL of H2O and aqueous washed with 100 mL of diethyl ether. The aqueous layer was then acidified with 1 mL of concentrated HCl (pH=1) and then extracted (2×100 mL) with diethyl ether and organic layers combined, dried over MgSO4, filtered and volatile components removed under reduced pressure to give 1.75 grams of the t-butyl thioether product which was used without any further purification.

1. additionAfter addition
2. customAfter 18 hours the volatile components of the reaction mixture were removed under reduced pressure
3. customto give a brown solid
4. washaqueous washed with 100 mL of diethyl ether
5. extractionextracted (2×100 mL) with diethyl ether and organic layers
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. customvolatile components removed under reduced pressure

ORD record

ord-20dcea2fb3304df5b7e7d48528542fbf

Source dataset

uspto-grants-1997_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05693720