Sodium Cyanide → Ethyl o-cyanomethylcinnamate

HRID 26621Notes

Reaction equation

HRID 26621 reaction equation
Br[CH2:2][C:3]1[CH:15]=[CH:14][CH:13]=[CH:12][C:4]=1[CH:5]=[CH:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].[C-:16]#[N:17].[Na+]>C(O)C>[C:16]([CH2:2][C:3]1[CH:15]=[CH:14][CH:13]=[CH:12][C:4]=1[CH:5]=[CH:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])#[N:17]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 54228366Ethyl 3-[2-(bromomethyl)phenyl]prop-2-enoate

Product 1

HCID 53697120Ethyl o-cyanomethylcinnamate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl o-(bromomethyl)cinnamate (94.1 g., 0.35 mole), and sodium cyanide (20.6 g., 0.42 mole) in ethanol (450 ml.) is heated at reflux for 3 hours. About half of the ethanol is removed at reduced pressure. To the residue is added 500 ml. of water. The oily product is taken up in ether, washed with water, and dried over magnesium sulfate. Evaporation of the ether affords the title compound as an oil.

Workup

  1. temperatureat reflux for 3 hours
  2. customAbout half of the ethanol is removed at reduced pressure
  3. additionTo the residue is added 500 ml
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of the ether

Sources & evidence

ORD record
ord-ef18fa6e636b4f14876fac19aacec3d6
Source dataset
uspto-grants-1979_04
Patent number
US04150235

Reaction notes

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