Water → 78016-72-5

Temperature

-5 °C

2-Ethylhexanol (50.51 g, 0.384 mol) and pyridine (260 mL) are combined in a flask fitted with a condenser, internal thermometer, mechanical stirrer and argon inlet. The solution is cooled to -5° C. and to it is added p-toluenesulfonyl chloride (89.63 g, 0.416 mol) in portions via Gooch tubing so as to maintain the reaction temperature -5°-5° C. After 3 h, water (40 mL) is added in portions so as to keep the temperature of the reaction below 5° C. The reaction mixture is warmed to room temperature and then poured into a separatory funnel containing 540 mL of ether. The layers are separated and the organic layer is washed with 5M H2SO4 (2×140 mL), saturated CuSO4 solution (140 mL), water (2×140 mL) and saturated NaHCO3 solution (140 mL). After drying over MgSO4, the organic layer is filtered, and concentrated to leave a light yellow liquid as 2-ethyhexanyl p-toluenesulfonate. Purity of the product is determined by thin layer chromatography and the structure confirmed by 1H and 13C NMR.

1. customfitted with a condenser
2. temperatureto maintain the reaction temperature -5°-5° C
3. customthe temperature of the reaction below 5° C
4. temperatureThe reaction mixture is warmed to room temperature
5. additionpoured into a separatory funnel
6. customThe layers are separated
7. washthe organic layer is washed with 5M H2SO4 (2×140 mL), saturated CuSO4 solution (140 mL), water (2×140 mL) and saturated NaHCO3 solution (140 mL)
8. dry with materialAfter drying over MgSO4
9. filtrationthe organic layer is filtered
10. concentrationconcentrated

ORD record

ord-e4723da81e344e8f869879d4744fb30f

Source dataset

uspto-grants-1998_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05716918