Toluene → ethyl 2-cyano-3-(2-methylphenyl)acrylate

HRID 469264Notes

Reaction equation

HRID 469264 reaction equation
[CH2:1]([O:3][C:4](=[O:8])[CH2:5][C:6]#[N:7])[CH3:2].N1CCCC[CH2:10]1.[C:15]1([CH3:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[C:6]([C:5](=[CH:21][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:10])[C:4]([O:3][CH2:1][CH3:2])=[O:8])#[N:7]

Participants

4

Reactant 3

HCID 1140TolueneHCID 7764Ethyl cyanoacetateHCID 8082Piperidine

Product 1

HCID 598431ethyl 2-cyano-3-(2-methylphenyl)acrylateYield 59%

Procedure

O-Tolylaldehyde (10 g, 83.2 mmol), ethylcyanoacetate (9.4 g, 83.2 mmol), and piperidine (1.1 mL, 11 mmol) were heated in toluene at reflux for 1 hour. The reaction was washed with H2O and brine, dried over MgSO4, and concentrated, with the resulting residue purified by chromatography (10-50% EtOAc, petroleum ether) to give ethyl 2-cyano-3-o-tolylacrylate (10.6 g, 59%).

Workup

  1. temperatureat reflux for 1 hour
  2. washThe reaction was washed with H2O and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated, with the resulting residue
  5. custompurified by chromatography (10-50% EtOAc, petroleum ether)

Sources & evidence

ORD record
ord-7e184a76c6d6429d8f9864109e7b689b
Source dataset
uspto-grants-2014_01
Patent number
US08629149B2

Reaction notes

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