반응 #409088

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1,3-Cyclohexanedicarboxylic acid

acetic anhydride

→

1

수율 93.6%

cis-1,3-Cyclohexanedicarboxylic Anhydride

수율 93.6%

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후처리

1. 1
   온도The resulting mixture was heated
2. 2
   온도to reflux (at which point it was homogeneous) for 5 h
3. 3
   workup.ADDITIONA distillation head was added
4. 4
   기타the volatiles were removed
5. 5
   workup.DISTILLATIONOnce no more distillate was collected the residue
6. 6
   온도was cooled to ambient temperature
7. 7
   기타to afford a solid mass
8. 8
   기타The crude product was recrystallized from hot toluene (40 mL) by the addition of heptane (40 mL)
9. 9
   온도cooling to 4° C
10. 10
    여과The precipitated product was filtered
11. 11
    세척washed with heptane
12. 12
    기타dried in vacuo

실험 절차

1,3-Cyclohexanedicarboxylic acid (mixture of cis and trans; 20 g; 0.116 mol) was slurried in acetic anhydride (80 mL; 0.85 mol; 7.3 equiv). The resulting mixture was heated to reflux (at which point it was homogeneous) for 5 h. A distillation head was added and the volatiles were removed by increasing the pot temperature to 200° C. Once no more distillate was collected the residue was cooled to ambient temperature to afford a solid mass. The crude product was recrystallized from hot toluene (40 mL) by the addition of heptane (40 mL) and cooling to 4° C. The precipitated product was filtered, washed with heptane, and dried in vacuo to afford 16.74 g (93%) of 1.

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