Ethyl o-cyanomethylcinnamate → Ethyl o-(cyanomethyl)hydrocinnamate

HRID 26622Notes

Reaction equation

HRID 26622 reaction equation
[C:1]([CH2:3][C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[CH:6]=[CH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])#[N:2].[H][H]>C(O)C.[Pd]>[C:1]([CH2:3][C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])#[N:2]

Participants

5

Reactant 2

HCID 53697120Ethyl o-cyanomethylcinnamateHCID 178418361HCID 178418361, compound

Product 1

HCID 54486935Ethyl o-(cyanomethyl)hydrocinnamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ethyl o-(cyanomethyl)cinnamate (75.1 g., 0.35 mole) is dissolved in ethanol (300 ml.) and hydrogenated at a pressure of 1 atmosphere and room temperature over 2.5 g. of a 5% palladium on charcoal catalyst. When the theoretical amount of hydrogen (0.35 mole) has been absorbed, the catalyst is filtered off and the ethanol removed by distillation at reduced pressure to yield ethyl o-(cyanomethyl)hydrocinnamate.

Workup

  1. customhydrogenated at a pressure of 1 atmosphere and room temperature over 2.5 g
  2. filtrationthe catalyst is filtered off
  3. customthe ethanol removed by distillation at reduced pressure

Sources & evidence

ORD record
ord-5534f8a9246b4596a60f669e7155d506
Source dataset
uspto-grants-1979_04
Patent number
US04150235

Reaction notes

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