Benzaldehyde → alpha-Cyanocinnamic acid ethyl ester

HRID 2240843Notes

Reaction equation

HRID 2240843 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:10].N1CCCCC1>CCO>[CH2:15]([O:14][C:12](=[O:13])/[C:11](/[C:9]#[N:10])=[CH:1]/[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:16]

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 7764Ethyl cyanoacetateHCID 8082Piperidine

Product 1

HCID 668187alpha-Cyanocinnamic acid ethyl esterYield 48.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of benzaldehyde (0.6 mol, 63.7 g), ethyl cyanoacetate (0.6 mol, 67.8 g) and piperidine (1 mL) in EtOH (60 mL) was stirred overnight. The clear solution was then placed in an ice-water bath to initiate the crystallization. The crystalline material was filtered, washed with EtOH and dried in a vacuum oven at 50° C. to give 58.27 g of (E)-2-cyano-3-phenyl-acrylic acid ethyl ester. The mother liquors and the washings were concentrated under reduced pressure; the residue was cooled in an ice-water bath to produce more crystalline product. This material was collected by filtration and washed with hexane, and a mixture EtOH/hexane (1/4), it was then dried in a vacuum oven at 63° C. to give 38.01 g of (E)-2-cyano-3-phenyl-acrylic acid ethyl ester (80% combined yield).

Workup

  1. customThe clear solution was then placed in an ice-water bath
  2. customthe crystallization
  3. filtrationThe crystalline material was filtered
  4. washwashed with EtOH
  5. customdried in a vacuum oven at 50° C.

Sources & evidence

ORD record
ord-9feb3201123c4695a578571214766dee
Source dataset
uspto-grants-2010_05
Patent number
US07723391B2

Reaction notes

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