Potassium Cyanide → Ethyl 3-cyano-3-phenylpropanoate

HRID 45244Notes

Reaction equation

HRID 45244 reaction equation
[CH:1](=[C:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])C(OCC)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:19]#[N:20].[K+]>CCO.O>[C:19]([CH:1]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:8][C:14]([O:16][CH2:17][CH3:18])=[O:15])#[N:20]

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 94751Diethyl (phenylmethylene)malonate

Product 1

HCID 12414061Ethyl 3-cyano-3-phenylpropanoateYield 83%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 64 g (257.8 mmol) of diethyl benzylidenepropanedioate and 17 g (261 mmol) of potassium cyanide in 750 mL of EtOH and 75 mL of water is heated for 18 hours at 60° C. The medium is then concentrated under reduced pressure and taken up in 500 mL of brine and then extracted with Et2O (2×500 mL). The organic phases are dried over Na2SO4, filtered and then concentrated under reduced pressure. 43.5 g of ethyl 3-cyano-3-phenylpropanoate are obtained in the form of a solid, which is used without further purification in the following step.

Workup

  1. concentrationThe medium is then concentrated under reduced pressure
  2. extractionextracted with Et2O (2×500 mL)
  3. dry with materialThe organic phases are dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5573ee57bf374732b420222de8048606
Source dataset
uspto-grants-2013_09
Patent number
US08541455B2

Reaction notes

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