反应详情

温度

-15 °C

In a three necked round bottom flask were combined 28 ml of methanol and 38 ml of water. The solution was cooled to -15° C. and 0.166 mole of 5-methyl-2-(2-hydroxy-propyl)furan (J. Org. Chem., 26, 1673, 1960) and 0.416 mole of chlorine were added simultaneously. During the addition, the reaction was maintained between -16° and -8° C. When addition was completed, the solution was warmed to 80° C. and refluxed for about 3 hours. Upon cooling to room temperature, the pH was adjusted to 2.1 and extracted with chloroform (3×100 ml). The combined organic layers were washed with water, brine and dried over magnesium sulfate. The organic solution was filtered and evaporated to give a thick dark solid. The solid was recrystallized twice from methanol to give 8.06 grams (30% yield) of white solid. Sublimation yielded pure product, m.p. 157°-159° C.

1. additionDuring the addition
2. temperaturethe reaction was maintained between -16° and -8° C
3. additionWhen addition
4. temperaturethe solution was warmed to 80° C.
5. temperaturerefluxed for about 3 hours
6. temperatureUpon cooling to room temperature
7. extractionextracted with chloroform (3×100 ml)
8. washThe combined organic layers were washed with water, brine
9. dry with materialdried over magnesium sulfate
10. filtrationThe organic solution was filtered
11. customevaporated
12. customto give a thick dark solid
13. customThe solid was recrystallized twice from methanol