Ethyl formate → 2-Formyl-2-phenylacetonitrile

HRID 1707036Notes

Reaction equation

HRID 1707036 reaction equation
[H-].[Na+].[C:3]1([CH2:9][C:10]#[N:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:12](OCC)=[O:13].[Na]>CCCCCC.C(O)C>[CH:12]([CH:9]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[C:10]#[N:11])=[O:13]

Participants

7

Reactant 4

HCID 8025Ethyl formateHCID 8794PhenylacetonitrileHCID 24758Sodium hydride2×HCID 5360545Sodium

Product 1

HCID 3458802-Formyl-2-phenylacetonitrile

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8058HexaneSolvent

Procedure

A 20.0 g. amount of sodium hydride (50% in oil) is added portionwise with stirring to a solution of 20.0 g. of phenylacetonitrile and 40.0 ml. of ethyl formate in 200 ml. of sodium dried benzene. The mixture is heated on a steam bath to start the reaction and after the vigorous reaction has subsided, the mixture is heated on the steam bath for 2 hours with stirring. Ethanol is then added dropwise to decompose the excess sodium hydride. The mixture is then swamped with n-hexane and the precipitate is collected and washed with n-hexane. The precipitate is suspended in water then an excess of dilute hydrochloric acid is added and the product is extracted with ether. The ether extracts are dried and evaporated. The residue is crystallized from acetone-n-hexane to give 12.0 g. of the product of the Example m.p. 161°-163° C. Reference: D. J. Brown and T. C. Lee, J. Chem. Soc. (C), 214 (1970).

Workup

  1. temperatureThe mixture is heated on a steam bath
  2. customthe reaction
  3. customafter the vigorous reaction
  4. temperaturethe mixture is heated on the steam bath for 2 hours
  5. stirringwith stirring
  6. customthe precipitate is collected
  7. washwashed with n-hexane
  8. additionan excess of dilute hydrochloric acid is added
  9. extractionthe product is extracted with ether
  10. dry with materialThe ether extracts are dried
  11. customevaporated
  12. customThe residue is crystallized from acetone-n-hexane
  13. customto give 12.0 g

Sources & evidence

ORD record
ord-8323f7c4cbd0452091ffb7ea3505e771
Source dataset
uspto-grants-1980_06
Patent number
US04209621

Reaction notes

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