Acetone → 2-Cyano-3-methyl-but-2-enoic acid ethyl ester

HRID 369454Notes

Reaction equation

HRID 369454 reaction equation
[CH2:1]([O:3][C:4](=[O:8])[CH2:5][C:6]#[N:7])[CH3:2].[CH3:9][C:10]([CH3:12])=O.N1CCCCC1>>[C:10](=[C:5]([C:6]#[N:7])[C:4]([O:3][CH2:1][CH3:2])=[O:8])([CH3:12])[CH3:9]

Participants

4

Reactant 3

HCID 180AcetoneHCID 7764Ethyl cyanoacetateHCID 8082Piperidine

Product 1

HCID 1365732-Cyano-3-methyl-but-2-enoic acid ethyl esterYield 82.3%

Conditions

Temperature
25 °C

Procedure

A mixture of 152 g (1.34 mole) of ethylcyanoacetate (3) in 152 g (2.62 mole) of acetone (2) containing 4 mL of piperidine was stirred at 20-30° C. for 16 hours then heated to reflux for 24 hours. Removing the volatile portion, the residue was distilled at 30-50μ of Hg. The fractions boiling at 56-67° C. were collected to give 169 g (82%) of a colorless oil.

Workup

  1. temperaturethen heated
  2. temperatureto reflux for 24 hours
  3. customRemoving the volatile portion
  4. distillationthe residue was distilled at 30-50μ of Hg
  5. customThe fractions boiling at 56-67° C. were collected

Sources & evidence

ORD record
ord-191d2d5935de480f83b1fe53a6117cd1
Source dataset
uspto-grants-2000_10
Patent number
US06136982

Reaction notes

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