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

HRID 46989Notes

Reaction equation

HRID 46989 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-5a2238bf2cb243deb54f41fa66ed13b8
Source dataset
uspto-grants-1979_11
Patent number
US04175203

Reaction notes

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