반응 #409092

반응 방정식

water

Anhydride

cis-1,3-Cyclohexanedicarboxylic Anhydride

isopropanol

p-Toluenesulfonic acid

→

Di-i-propyl cis-1,3-Cyclohexanedicarboxylate

용매

toluene

반응 조건

후처리

1. 1
   온도the reaction mixture was heated
2. 2
   workup.DISTILLATIONcould be continuously distilled
3. 3
   온도After 7 hr at reflux
4. 4
   세척The reaction mixture was washed with saturated aqueous sodium bicarbonate (2×10 mL)
5. 5
   건조The organic solution was dried over MgSO4
6. 6
   농축concentrated
7. 7
   기타to afford cis-2d which

실험 절차

Anhydride 1 (1.21 g; 7.8 mmol) was dissolved in isopropanol (6.0 mL; 78 mmol; 10 equiv) and toluene (6 mL). p-Toluenesulfonic acid (74 mg; 0.39 mmol; 0.05 equiv) was added and the reaction mixture was heated to reflux under conditions where water could be continuously distilled using a Dean-Stark trap. After 7 hr at reflux, GC analysis indicated >96% conversion to 2d. The reaction mixture was washed with saturated aqueous sodium bicarbonate (2×10 mL). The organic solution was dried over MgSO4 and concentrated to afford cis-2d which was a single peak by GC analysis.

출처