Methyl 2-cyano-3-phenyl-2-propenoate → HCID 53907581, compound

HRID 568183Notes

Reaction equation

HRID 568183 reaction equation
[CH3:1][CH:2]([OH:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH:10](=[C:17]([C:22]#[N:23])[C:18](OC)=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>[O-]CCCC.[O-]CCCC.[O-]CCCC.[O-]CCCC.[Ti+4].C1CCCCC1>[CH:10](=[C:17]([C:22]#[N:23])[C:18]([O:9][CH:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH3:1])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 19414Methyl 2-cyano-3-phenyl-2-propenoateHCID 200832-Octanol

Product 1

HCID 53907581HCID 53907581, compound

Reagents, catalysts & solvents 2

HCID 21801Titanium tetrabutoxideCatalystHCID 8078CyclohexaneSolvent

Conditions

Temperature
130 °C

Procedure

143.60 g 2-octanol, 206.40 g methyl benzylidenecyanoacetate, 211.70 g cyclohexane and 0.56 g titanium (IV) tetrabutoxide were charged to a flask fitted with an oil bath for heating. The oil bath was heated to 130° C. and methanol was removed as an azeotrope for a period of approximately 25 hours. The methyl benzylidenecyanoacetate used in this synthesis was made by mixing 1.198 kg benzaldehyde, 1.119 kg methyl cyanoacetate, 0.920 kg absolute ethanol and 0.66 g piperidine. The mixture is refluxed for two hours and allowed to cool. The resulting product was a mobile liquid that was ±2-octyl benzylidenecyanoacetate having a representative structure shown below.

Workup

  1. customfitted with an oil bath
  2. temperaturefor heating
  3. custommethanol was removed as an azeotrope for a period of approximately 25 hours
  4. additionby mixing 1.198 kg benzaldehyde, 1.119 kg methyl cyanoacetate, 0.920 kg absolute ethanol and 0.66 g piperidine
  5. temperatureThe mixture is refluxed for two hours
  6. temperatureto cool

Sources & evidence

ORD record
ord-c73c589f052646ec88b11e4d5cca0dd4
Source dataset
uspto-grants-2001_01
Patent number
US06180813B2

Reaction notes

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