Ethyl formate → 2-Formyl-2-phenylacetonitrile

HRID 621645Notes

Reaction equation

HRID 621645 reaction equation
C[O-].[Na+].[CH:4](OCC)=[O:5].[C:9]1([CH2:15][C:16]#[N:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1C=CC=CC=1>[CH:4]([CH:15]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:16]#[N:17])=[O:5]

Participants

5

Reactant 3

HCID 8025Ethyl formateHCID 8794PhenylacetonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 3458802-Formyl-2-phenylacetonitrile

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a suspension of sodium methoxide (5.56 g) in benzene (200 ml) is added dropwise with stirring a mixture of ethyl formate (8.14 g) and phenylacetonitrile (11.7 g) under ice cooling. After 30 minutes, the ice bath is taken off. After reacting for 3 hours, ice water is added to the reaction mixture, and the aqueous layer is separated. The organic layer is washed with 0.5 N sodium hydroxide solution (50 ml×3), and the aqueous layer and the washings are combined and adjusted to pH 3-4 with conc. hydrochloric acid. The mixture is stirred under ice cooling for 20 minutes, and the resulting precipitate is separated by filtration and washed with water to give α-formylphenylacetonitrile. The product is used in the subsequent procedure without further purification.

Workup

  1. additionis added dropwise
  2. waitAfter reacting for 3 hours
  3. customthe aqueous layer is separated
  4. washThe organic layer is washed with 0.5 N sodium hydroxide solution (50 ml×3)
  5. stirringThe mixture is stirred under ice cooling for 20 minutes
  6. customthe resulting precipitate is separated by filtration
  7. washwashed with water

Sources & evidence

ORD record
ord-a2c44c8e1ee345e0af81bb0a05d792ff
Source dataset
uspto-grants-1989_04
Patent number
US04824834

Reaction notes

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