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ChemicalBook CAS DataBase List n-Butyl cyanoacetate
5459-58-5

n-Butyl cyanoacetate synthesis

6synthesis methods
To a well-stirred mixture of cyano acid (80 mmol) in alcohol (90 mmol), and acetonitrile (162 mmol) , added sulfuric acid (98%, 94 mmol, 5 mL) at room temperature and temperature maintained between 80-85°C for 16-18h. The reaction mixture was cooled and added to 20% sodium carbonate solution (100 mL). The reaction mass was extracted in CH2Cl2 (50 mL × 2). The combined organic layer was washed with water (100 mL), dried over sodium sufate, and concentrated under reduced pressure to obtain n-Butyl cyanoacetate (85-95%).
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Yield:5459-58-5 95%

Reaction Conditions:

with sulfuric acid;acetonitrile at 80 - 85; for 16 - 18 h;

Steps:

Procedure for cyano acid (Table 2, entry 16b-21b):
General procedure: To a well-stirred mixture of cyano acid (80 mmol) in alcohol (90 mmol), and acetonitrile (162 mmol) , added sulfuric acid (98%, 94 mmol, 5 mL) at room temperature and temperature maintained between 80-85°C for 16-18h. The reaction mixture was cooled and added to 20% sodium carbonate solution (100 mL). The reaction mass was extracted in CH2Cl2 (50 mL × 2). The combined organic layer was washed with water (100 mL), dried over sodium sufate, and concentrated under reduced pressure to obtain product (85-95%). Most example gave NMR pure product. Where minor impurities are formed, the product was purified over silica gel using ethyl acetate: petroleum ether (1:9).

References:

Dawar, Pankaj;Raju, M. Bagavan;Ramakrishna, Ramesha Andagar [Synthetic Communications,2014,vol. 44,# 6,p. 836 - 846] Location in patent:supporting information

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