反応 #2460286

反応方程式

2-butynedioic acid

n-butyl alcohol

sulfuric acid

→

dibutyl acetylenedicarboxylate

反応条件

後処理

1. 1
   温度was heated
2. 2
   温度at reflux for 6 hours
3. 3
   温度The mixture was cooled to ambient,
4. 4
   洗浄washed with 10% aqueous NaHCO3
5. 5
   乾燥with brine, dried (Na2SO4)
6. 6
   濃縮concentrated
7. 7
   workup.DISTILLATIONthe resulting crude product distilled under reduced pressure (bp 65-70° C./0.08 mm)
8. 8
   その他Dibutyl acetylenedicarboxylate was obtained as a colorless oil (8.5 g, 86% of theory)

実験手順

First, dibutyl acetylenedicarboxylate was prepared. A mixture of 2-butynedioic acid (5.0 g, 44 mmol), n-butyl alcohol (162 g, 2.19 mol), and sulfuric acid (0.86 g, 9 mmol) was heated at reflux for 6 hours. The mixture was cooled to ambient, washed with 10% aqueous NaHCO3 then with brine, dried (Na2SO4), concentrated, and the resulting crude product distilled under reduced pressure (bp 65-70° C./0.08 mm). Dibutyl acetylenedicarboxylate was obtained as a colorless oil (8.5 g, 86% of theory). 1H NMR (CDCl3): δ 1.90 (t, 6H), 1.38 (m, 4H), 1.65 (m, 4H), 4.20 (t, 4H).

出典