反应详情

温度

10 °C

To a solution of 180 g of 2-Isopropyl-4-methoxy-phenol (1.084 moles) in 2.5 L toluene was added 206.7 g p-toluene sulfonylchloride (1.084 moles), and the reaction mixture was stirred vigorously The resultant mixture was cooled to 10° C., and triethylamine (3 mol) was gradually added, keeping the temperature below 50 degrees C. The reaction mixture was aged for 3 hours at approximately 50° C. and then allowed to cool to RT. An HPLC sample obtained at this point showed completion of the reaction. The resultant suspension was filtered and the filter-cake was washed with 300 mL toluene. The collected filtrate was distilled under vacuum until the pot-temperature reached 65° C., and 1 L of methanol was added to the mixture. The methanolic solution was stirred for 30 minutes at reflux; then the mixture was permitted to cool overnight. The white crystalline solid which separated was collected by filtration and dried at 50° C. under vacuum to yield a total of 332 grams of toluene-4-sulfonic acid 2-isopropyl-4-methoxy-phenyl ester, representing an yield of 95.7%:m.p. 85.1 degrees C.

1. customthe temperature below 50 degrees C
2. temperatureto cool to RT
3. customAn HPLC sample obtained at this point
4. customcompletion of the reaction
5. filtrationThe resultant suspension was filtered
6. washthe filter-cake was washed with 300 mL toluene
7. distillationThe collected filtrate was distilled under vacuum until the
8. custompot-temperature reached 65° C.
9. addition1 L of methanol was added to the mixture
10. temperatureat reflux
11. temperatureto cool overnight
12. customThe white crystalline solid which separated
13. filtrationwas collected by filtration
14. customdried at 50° C. under vacuum