반응 #155414

반응 방정식

2-methyltetrahydrofuran

benzene-1,3-dithiol

2-methyltetrahydrofuran

dimethylsulfate

2-methyltetrahydrofuran

sodium hydroxide

→

title compound

수율 78.0%

3-(Methylthio)benzenethiol

수율 78.0%

용매

tert-butylmethylether

반응 조건

후처리

1. 1
   온도The resulting solution was cooled to between 0° C. and 5° C.
2. 2
   온도wise maintaining the temperature of the reaction mixture below 15° C.
3. 3
   온도After cooling to ambient temperature the resulting solution
4. 4
   기타the phases were separated
5. 5
   추출The organic phase was extracted with sodium hydroxide (2 M aqueous solution, 250 mL)
6. 6
   온도the combined aqueous phases were cooled to 10° C.
7. 7
   workup.ADDITIONhydrochloric acid (6M aqueous solution, 500 mL) was added
8. 8
   온도whilst maintaining the temperature of the mixture below 25° C
9. 9
   추출The resulting solution was extracted with tert-butylmethylether (2-fold 250 mL)
10. 10
    세척the combined organic phases were washed with water (500 mL)
11. 11
    농축concentrated in vacuo

실험 절차

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.

출처