反応 #40271

反応方程式

potassium cyanide

ethyl cyanoacetate

isovaleraldehyde

hexane

potassium cyanide

→

2-isobutyl-succinonitrile

収率 99.0%

溶媒

water

water

反応条件

後処理

1. 1
   その他When no additional water was collected
2. 2
   温度the mixture was cooled
3. 3
   workup.DISTILLATIONdistilled under vacuum
4. 4
   その他to remove solvent
5. 5
   workup.ADDITIONIsopropanol (1 L) was added to the remaining oil
6. 6
   workup.DISTILLATIONThe reaction mixture was distilled at atmospheric pressure until a temperature of 95° C.
7. 7
   温度refluxed at this temperature for 5 h
8. 8
   温度The reaction mixture was cooled
9. 9
   workup.ADDITIONdiluted with water (0.5 L)
10. 10
    抽出extracted with 1 L methyl tert-butyl ether (MTBE)
11. 11
    抽出The MTBE extract
12. 12
    洗浄was washed with water (0.5 L)
13. 13
    乾燥dried over anhydrous magnesium sulfate
14. 14
    ろ過filtered
15. 15
    濃縮concentrated under vacuum

実験手順

A mixture of ethyl cyanoacetate (73.3 g, 6.48 mol), isovaleraldehyde (613.9 g, 7.13 mol), piperidine (5.5 g, 0.065 mol), and hexane (0.5 L) was placed under reflux with continuous removal of water. When no additional water was collected, the mixture was cooled and distilled under vacuum to remove solvent. Isopropanol (1 L) was added to the remaining oil, followed by a solution of potassium cyanide (422 g, 6.48 mol) in water (2 L). The reaction mixture was maintained below 35° C. during addition of the potassium cyanide solution and then held at approximately 35° C. for 4 h. The reaction mixture was distilled at atmospheric pressure until a temperature of 95° C. was reached and then refluxed at this temperature for 5 h. The reaction mixture was cooled, diluted with water (0.5 L) and extracted with 1 L methyl tert-butyl ether (MTBE). The MTBE extract was washed with water (0.5 L), dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum to give 873.4 g of 2-isobutyl-succinonitrile as an oil. Purified samples of 2-isobutyl-succinonitrile can be obtained by vacuum distillation (90° C. at 0.275 mm Hg).

出典