Water → p-Toluenesulfonic acid (S)-2-methylbutyl ester

To a ice-cooled solution of p-toluenesulphonyl chloride (9.53 g, 50 mmol), (S)-2-methylbutan-1-ol (4.41 g, 50 mmol) in absolute dichloromethane (200 ml), triethylamine (84 ml) was dropwise added. After complete addition and stirring for further 6 h at room temperature, the reaction mixture was poured into water (150 ml), the organic layer was separated and the aqueous phase was further extracted with dichloromethane (2×200 ml). The combined organic extracts were washed with HCl 1N (2×200 ml), with saturated NaCl solution (2×200 ml), dried over magnesium sulphate and evaporated under reduced pressure. The obtained slightly yellow oil was chromatographed on silica (diethylether/petroleumether: 1/3) to give (s)-2-methyl-butyl p-toluenesulphonate as a colourless oil (Yield: 10.0 g, 89%).

1. additionwas dropwise added
2. additionAfter complete addition
3. customthe organic layer was separated
4. extractionthe aqueous phase was further extracted with dichloromethane (2×200 ml)
5. washThe combined organic extracts were washed with HCl 1N (2×200 ml), with saturated NaCl solution (2×200 ml)
6. dry with materialdried over magnesium sulphate
7. customevaporated under reduced pressure
8. customThe obtained slightly yellow oil
9. customwas chromatographed on silica (diethylether/petroleumether: 1/3)

ORD record

ord-efcbd2ff430b4b4ea7b9258da4f85fcd

Source dataset

uspto-grants-2003_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06534135B1