反应详情

温度

20 °C

To a cold (0°-5° C.) suspension of 4-(1,1-dimethylethyl)phenol (7.5 g., 0.05 mole) and phosphorous oxychloride (8 ml.) in 70% perchloric acid (10 ml.) is added dimethylsulfoxide (3.9 g., 0.05 mole) dropwise with vigorous stirring. The resulting reaction mixture is stirred at 0°-5° C. for 1 hour and at 20° C. for 16 hours and then poured onto crushed ice whereupon a gum separates. Upon warming to 20° C. with vigorous stirring there is obtained a white solid which is collected, washed with cold water, air dried at 20° C. with aspiration and washed with ether. The white solid (10 g., m.p. 160° C.) is added to saturated aqueous potassium chloride (100 ml.) and the resulting mixture, heated at reflux for 4 hours. After standing at 20° C. for 12 hours, the reaction mixture is extracted with ether. The ethereal extract is washed with water and saturated brine, dried over sodium sulfate and filtered. Evaporation of the filtrate in vacuo leaves 2-methylthio-4-(1,1-dimethylethyl)phenol as an analytically pure, colorless oil (5.7 g., 58%).

1. customThe resulting reaction mixture
2. additionpoured
3. customonto crushed ice whereupon a gum
4. temperatureUpon warming to 20° C.
5. stirringwith vigorous stirring there
6. customis obtained a white solid which
7. customis collected
8. washwashed with cold water, air
9. customdried at 20° C. with aspiration
10. washwashed with ether
11. additionThe white solid (10 g., m.p. 160° C.) is added to saturated aqueous potassium chloride (100 ml.)
12. temperaturethe resulting mixture, heated
13. temperatureat reflux for 4 hours
14. waitAfter standing at 20° C. for 12 hours
15. extractionthe reaction mixture is extracted with ether
16. extractionThe ethereal extract
17. washis washed with water and saturated brine
18. dry with materialdried over sodium sulfate
19. filtrationfiltered
20. customEvaporation of the filtrate in vacuo