反应详情

温度

50 °C

A solution of benzene-1,3-dithiol (50 g, 0.351 mmol) in 2-methyltetrahydrofuran (375 mL, 0.351 mmol) was treated with dimethylsulfate (33.3 mL, 0.351 mol) followed by 2-methyltetrahydrofuran (25 mL, used as line wash). The resulting solution was cooled to between 0° C. and 5° C. and sodium hydroxide (2M aqueous solution, 210.6 mL) was added drop wise maintaining the temperature of the reaction mixture below 15° C. followed by 2-methyltetrahydrofuran (25 mL, used as line wash) and heated under nitrogen to 50° C. for 4 hours. After cooling to ambient temperature the resulting solution was treated with tert-butylmethylether (500 mL) and the phases were separated. The organic phase was extracted with sodium hydroxide (2 M aqueous solution, 250 mL) and the combined aqueous phases were cooled to 10° C. and hydrochloric acid (6M aqueous solution, 500 mL) was added whilst maintaining the temperature of the mixture below 25° C. The resulting solution was extracted with tert-butylmethylether (2-fold 250 mL) and the combined organic phases were washed with water (500 mL) and concentrated in vacuo to give the title compound as a yellow oil, 78% yield, 42.9 g.

1. temperatureThe resulting solution was cooled to between 0° C. and 5° C.
2. temperaturewise maintaining the temperature of the reaction mixture below 15° C.
3. temperatureAfter cooling to ambient temperature the resulting solution
4. customthe phases were separated
5. extractionThe organic phase was extracted with sodium hydroxide (2 M aqueous solution, 250 mL)
6. temperaturethe combined aqueous phases were cooled to 10° C.
7. additionhydrochloric acid (6M aqueous solution, 500 mL) was added
8. temperaturewhilst maintaining the temperature of the mixture below 25° C
9. extractionThe resulting solution was extracted with tert-butylmethylether (2-fold 250 mL)
10. washthe combined organic phases were washed with water (500 mL)
11. concentrationconcentrated in vacuo